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Tax benefits when one LLC rents property from another LLC with same owner - legal structure question

About five years ago, I worked for a marketing agency that operated as an LLC. The interesting part was that this marketing LLC actually rented their downtown office space from a separate real estate LLC. What caught my attention was that both LLCs were owned by the same individual entrepreneur. I thought this was a pretty clever arrangement for liability protection and possibly tax advantages. The marketing LLC was paying rent to the real estate LLC, and since they were separate entities, it seemed like each business was protected from the other's potential liabilities. I'm now considering setting up something similar with my own businesses. I'm planning to start a car rental service through a platform like Turo with 2-3 vehicles. I'm also thinking about creating a separate LLC that would own a small parking lot. The rental LLC would then pay the parking lot LLC for storing the vehicles when they're not being rented out. This way, the car rental business could expense the parking fees, while those same fees would help cover the mortgage on the parking lot property. But I'm confused about how this actually works from a tax and legal perspective. Does this arrangement actually provide tangible benefits when both LLCs have the same owner? Are there potential issues with the IRS viewing this as some kind of tax avoidance scheme? And is there a way to structure this that's both legal and advantageous? Would I be creating some kind of circular income situation? Or are there legitimate advantages to having my car rental LLC pay my parking lot LLC?

NebulaNinja

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This has been such an educational thread! As someone new to business structures, I'm amazed by the depth of practical experience shared here. The progression from basic liability protection concepts to detailed operational considerations like seasonal cash flow management and exit strategies really shows how complex these decisions can be. One aspect that strikes me is how much the success of these structures depends on treating them as genuine business relationships rather than just tax planning vehicles. The emphasis on market-rate documentation, proper invoicing, and arm's length dealings seems to be the common thread through everyone's experiences. I'm particularly interested in the point @Marcelle Drum made about lenders potentially discounting related-party rental income. That's exactly the kind of real-world consideration that could affect financing decisions down the road. It sounds like having extensive documentation and market rate analyses becomes even more important when you need to demonstrate economic substance to third parties. For those just starting out like myself, it seems like the key takeaway is that while these structures can provide significant benefits, they require a serious commitment to proper administration and documentation. The quarterly compliance reviews and systematic record-keeping that several people mentioned seem essential for maintaining the integrity of the arrangement over time. Thanks to everyone who shared their experiences - this discussion has given me a much clearer picture of both the opportunities and responsibilities involved in multi-LLC structures. The community's willingness to share detailed practical insights makes this such a valuable resource for navigating complex business decisions!

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AstroAlpha

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Welcome to the community @NebulaNinja! You've really captured the essence of what makes these multi-LLC structures work - it's all about genuine business substance rather than just creative tax planning. As someone who's also relatively new to complex business structures, I've been taking notes throughout this entire discussion. The consistent theme seems to be that documentation and arm's length treatment aren't just nice-to-haves, they're absolutely essential for maintaining both legal protection and tax advantages. What I find particularly valuable is how everyone has emphasized the long-term perspective. It's easy to focus on the immediate benefits like liability protection and tax deductions, but understanding how these structures affect lending, exit strategies, and even day-to-day operations is crucial for making informed decisions. I'm curious about one practical aspect that hasn't been fully explored - when you're just getting started with a business like car rentals, how do you balance the desire for proper structure with the reality of limited initial cash flow? The administrative costs, separate accounting systems, and professional fees for setup and maintenance could be significant for a new business owner. Has anyone here started with a simpler structure initially and then evolved to the multi-LLC approach as their business grew? I'm wondering if there's a practical threshold where the benefits clearly outweigh the complexity and costs. Thanks to everyone for sharing such detailed real-world experiences - this thread should be required reading for anyone considering multi-entity business structures!

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Welcome to the community! This thread has been incredibly comprehensive and educational. As someone just starting to explore multi-entity structures, I'm struck by how much the success really depends on treating these arrangements as legitimate business relationships from day one. One question I haven't seen addressed is the timing of cash flows between entities. In a car rental business, you might receive payments from Turo at irregular intervals, but your parking lot LLC probably has regular monthly expenses. How do you handle situations where the timing doesn't align? For instance, if Turo payments are delayed but your parking lot mortgage is due, can the rental LLC pay late without creating documentation issues, or do you need to maintain strict monthly payment schedules regardless of cash flow timing? Also, I'm curious about the scalability aspect. If you start with 2-3 vehicles and later expand to 10-15 vehicles, would you need to adjust the rental rates to reflect the increased usage of the parking space? And how do you document those adjustments to maintain the arm's length character of the arrangement? The liability protection benefits are compelling, but I want to make sure I understand all the operational nuances before committing to this structure. Thanks to everyone who has shared such detailed real-world experiences - this discussion has been more valuable than any formal consultation I've had!

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This has been such an incredibly thorough discussion! As someone who's been curious about this topic after hearing it mentioned in various financial discussions, I really appreciate how everyone has broken down the complexity behind what seemed like a simple concept. What's really eye-opening is discovering that "net taxpayer" isn't an official IRS term at all, but rather gets used in different contexts with different meanings - from economic policy discussions to informal accounting usage. It explains why I was having such a hard time finding consistent definitions when I tried to research this myself. The consensus here seems clear: instead of getting caught up in trying to calculate whether you fit some ambiguous label, focus on understanding and optimizing your actual tax situation. The practical advice about tracking effective tax rates, maximizing deductions and credits, and making tax-informed financial decisions is so much more valuable than chasing after a classification that changes depending on how you define it. I'm also taking away a healthy skepticism about financial terminology that gets thrown around in media without precise definitions. This discussion has been a great reminder to dig deeper into concepts rather than accepting them at face value. Thanks to everyone who shared their expertise - this community continues to be an amazing resource for cutting through financial complexity and getting to actionable insights!

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Cole Roush

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This has been absolutely fascinating to read through! As someone new to this community, I'm impressed by how a seemingly straightforward question about "net taxpayer" status turned into such a comprehensive exploration of tax policy, economics, and practical financial planning. What really stands out to me is how this discussion perfectly illustrates why it's so important to question the financial terminology we encounter in media and political discourse. The fact that "net taxpayer" has no official IRS definition but gets used so widely in different contexts really drives home the need to dig deeper rather than accepting concepts at face value. The shift throughout this thread from trying to define the term to focusing on actionable tax optimization strategies has been incredibly valuable. I'm definitely going to implement some of the practical advice shared here - tracking my effective tax rate over time, using the IRS Interactive Tax Assistant to identify potential deductions, and thinking more strategically about tax-advantaged account contributions. It's also been enlightening to see how much someone's tax position can change based on life circumstances. It really reinforces that tax planning should be an ongoing process rather than trying to fit into fixed categories that may not even be meaningfully defined. Thanks to everyone who contributed their knowledge and experience - this is exactly the kind of thoughtful discussion that makes this community such a valuable resource for financial education!

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Andre Dupont

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This has been such an educational thread! As someone who's been trying to understand my own tax situation better, I really appreciate how everyone has broken down the complexities behind the "net taxpayer" concept. What strikes me most is how this term gets thrown around in political and economic discussions as if it's a precise, well-defined metric, when in reality it's quite ambiguous and context-dependent. The lack of an official IRS definition really explains why I was getting conflicting information when I tried to research this topic myself. The practical takeaways here are invaluable. Instead of worrying about whether I technically qualify as a "net taxpayer," I should focus on understanding my effective tax rate, maximizing available deductions and credits, and making informed financial decisions with tax implications in mind. These are concrete actions that actually impact my financial situation, unlike trying to calculate my status in a category that shifts depending on how you define it. I'm particularly grateful for the insights about how dramatically someone's tax position can change based on life events like marriage, having children, or buying a home. It really reinforces that tax planning should be viewed as an ongoing process rather than a fixed classification. Thanks to everyone who shared their expertise - this discussion has given me a much clearer framework for thinking about my relationship with the tax system!

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Thank you all for sharing these solutions! I'm dealing with this exact same issue right now and was getting so frustrated. I tried the search method that Mason suggested - typed "taxable grants" in the search box and it took me directly to the right screen under Miscellaneous Income. One thing I wanted to add for anyone else following this thread: make sure you have your 1099-G handy when you do this because the software will ask you to verify the issuing agency information. It wants to match what you're entering with the form details, which makes sense for audit purposes. Also wanted to confirm what the tax preparer said earlier - I checked my completed return preview and the grant income does indeed show up on Schedule 1, Line 8z with the description I entered. It's reassuring to see it's going to the right place on the actual tax forms even though the software pathway is so buried. Really appreciate this community helping each other out during tax season! This thread probably saved dozens of people hours of frustration.

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This thread has been a lifesaver! I just went through the same frustrating experience trying to find where to enter my 1099-G Box 6 grant income. I ended up using the search method - typed "grants" and it took me right to the Miscellaneous Income section where I could enter the amount. One tip I'd add for newcomers like me: don't panic if your version of H&R Block looks slightly different than what others describe. I was using the online version and some of the menu paths were a bit different, but the search function worked the same way. The key is that grants from Box 6 always go under "Other Income" or "Miscellaneous Income" regardless of which pathway you take to get there. Also wanted to say thanks to everyone who explained the different methods - having multiple options really helps since not everyone's software version is exactly the same!

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Sienna Gomez

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I'm so glad I found this thread! I've been pulling my hair out for the past two days trying to figure out where to enter my 1099-G Box 6 grant income in H&R Block Premium. The software kept pushing me toward unemployment compensation sections and I was starting to think there was a bug. After reading through all these solutions, I tried the search method first - typed "taxable grants" in the search box and boom! It took me directly to the right input screen under Miscellaneous Income. Entered my $3,200 grant amount with the description "1099-G Box 6 Taxable Grant" and everything looks correct on the return preview. What's frustrating is that this should be more straightforward given how common grants have become, especially with all the COVID relief programs. But I'm grateful for this community sharing all these different approaches - the search function, the "Other Income" menu pathway, and even that hidden link in the unemployment section that someone mentioned. For anyone else struggling with this: don't give up! The income does need to be reported, but there are multiple ways to get to the right place in the software. The search function was definitely the fastest method for me.

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Lourdes Fox

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I'm so relieved to find this thread! I've been in the exact same situation - got a 1099-G with grant income in Box 6 and H&R Block kept steering me toward unemployment sections. I was starting to worry I'd have to switch to a different tax software entirely. Just tried the search method you mentioned and it worked like a charm! Typed "grants" and it took me straight to the Miscellaneous Income section. Got my $2,800 grant entered with the proper description and can see it showing up correctly on Schedule 1 in the preview. You're absolutely right about grants becoming more common - I never had to deal with this before receiving disaster relief grants last year. It's wild that such a straightforward reporting requirement is buried so deep in the software interface. Thanks to everyone in this thread for sharing so many different solutions!

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One consideration I haven't seen mentioned yet is the potential impact of state taxes on your jewelry sales. While everyone's focused on federal tax implications (which are definitely important), some states have different rules for inherited property or collectibles. Also, if you're planning to sell a significant amount, you might want to spread the sales across multiple tax years to manage your overall tax bracket. Since jewelry is considered a collectible and taxed at potentially higher rates (up to 28% as someone mentioned), large gains in a single year could push you into higher brackets. For the organizational challenge you mentioned with all those containers scattered around the house, I'd suggest tackling one room or area at a time and creating a basic inventory system. Even something as simple as numbering containers and keeping a master list can help you stay organized and ensure nothing gets overlooked. Don't forget that selling inherited items also means you might need to consider any estate tax implications if the total estate was large, though that probably doesn't apply to most situations given current exemption levels.

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Emma Davis

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This is a really good point about state taxes that I hadn't considered! I'm in California and just realized I should probably look into whether there are any specific state rules for inherited collectibles. Do you happen to know if most states just follow the federal step-up basis rules, or do some have their own requirements for inherited property? The idea about spreading sales across tax years is smart too. We're definitely looking at selling quite a bit, so managing the timing could help with the tax burden. I'm assuming there's no requirement to sell everything within a certain timeframe after inheriting it? And thank you for the organizational tip! We've been feeling completely overwhelmed by the sheer volume, so tackling it room by room sounds much more manageable than trying to deal with everything at once.

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Most states do follow the federal step-up basis rules, but there can definitely be variations in how they tax capital gains from collectibles. California, for example, doesn't have preferential capital gains rates like the federal government does, so you'd pay your regular state income tax rate on any gains. Some states have no capital gains tax at all, while others have specific exemptions or different treatment for inherited property. I'd definitely recommend checking with a tax professional familiar with California law, or at least reviewing the state tax forms to see how they handle inherited collectibles. The differences might not be huge for smaller amounts, but could add up if you're selling significant value. And no, there's typically no deadline for when you have to sell inherited items! You can take your time and spread sales out strategically. Just keep good records of when items were inherited versus when they were sold, since that affects which tax year the gains get reported in. Breaking it down room by room really does help psychologically too - makes the whole project feel less overwhelming when you can see actual progress being made.

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Emma Swift

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One thing I'd add to this great discussion is the importance of keeping detailed photos not just for documentation, but also for insurance purposes while you're going through the sorting process. With such a large collection scattered around, you want to make sure you're covered if anything happens before you can properly secure or sell valuable pieces. Also, since you mentioned the collection was disorganized and stored in various containers throughout the house, be sure to check for any hidden compartments in jewelry boxes or cases. I helped a friend clean out her aunt's estate and we found several valuable pieces tucked away in secret drawers and hidden compartments that we almost missed. For the overwhelming volume you're dealing with, consider setting up a simple sorting system: one area for obviously valuable pieces that need professional attention, another for signed costume jewelry that might be worth researching, and a third for clear costume pieces that can be sold in bulk lots. This can help you prioritize your time and energy on the items most likely to have significant value. The step-up basis everyone's discussed really does simplify the tax side considerably compared to other types of inherited assets. Just make sure you're documenting your process as you go - future you will thank you when tax season arrives!

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This is really smart advice about insurance coverage during the sorting process! I hadn't even thought about that risk. With everything scattered around, we definitely need to make sure we're protected while we figure out what's actually valuable. The tip about hidden compartments is fascinating - I'll definitely need to check all the jewelry boxes more carefully. We've been so focused on the obvious pieces that we might have missed some hidden treasures. Your sorting system makes perfect sense too. Right now everything feels equally overwhelming, but breaking it down into those three categories (valuable, research-worthy, and bulk costume) would help us focus our energy where it matters most. One question - when you mention documenting "your process," do you mean just keeping records of what we find and where, or something more detailed for tax purposes?

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Mei Liu

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I'm so sorry for your loss, Natasha. Dealing with tax paperwork while grieving is never easy. The advice here is spot on - you'll sign YOUR name on the signature line, not your aunt's. Write "Personal Representative" in the occupation field, and make sure to write "DECEASED" with the date of death (November 2024) across the top of the form. Since you mentioned you weren't court-appointed but are handling her affairs as the only living relative, you should definitely include Form 56 with the return to notify the IRS of your fiduciary role. This protects you and establishes your authority to act on her behalf. For her final return, you'll report all income she received from January 1, 2024 through her date of death in November. The interest, pension, and Social Security income you mentioned will all go on the regular lines of Form 1040. If there's a refund due, you'll likely need Form 1310 to claim it since you're not a surviving spouse. Take your time with this - the IRS generally allows up to 3 years from the original due date to file a final return, so there's no need to rush and make mistakes. You're doing a loving thing by handling her final affairs properly.

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Liam Mendez

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This is really comprehensive advice, thank you Mei! I'm new to this community and dealing with my grandfather's final tax return. One thing I'm still confused about - if I need to file Form 1310 to get his refund, do I file that at the same time as the 1040, or do I wait until after the return is processed? Also, is there a specific deadline for filing the final return, or just the normal April 15th deadline that would have applied to him?

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Ethan Brown

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Hi Liam! You'll file Form 1310 at the same time as the 1040 - attach it to the tax return when you mail it in. Don't wait until after processing, as the IRS needs it to authorize releasing the refund to you as a non-spouse representative. For the deadline, the final return follows the same filing deadline that would have applied to your grandfather. So if he normally filed by April 15th, that's still the deadline for his final return (April 15, 2025 for the 2024 tax year). However, if you need more time, you can file for an extension using Form 4868, which gives you until October 15th to file the actual return. One important note - even though you have until the normal deadline to file, if there are any taxes owed, interest and penalties can still accrue from the original due date. So if you think taxes are owed, it's better to file sooner rather than later, or at least make an estimated payment by the April deadline. Hope this helps with your grandfather's return!

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I'm sorry for your loss, Natasha. Having handled my grandmother's final return last year, I understand how overwhelming this can feel when you're already dealing with grief. The key points others have covered are correct - you'll sign YOUR name on the signature line (not your aunt's), write "Personal Representative" in the occupation field, and mark "DECEASED" with her date of death at the top of the form. One thing I wish someone had told me earlier: keep detailed records of everything you do related to her estate, including copies of the tax return and any correspondence with the IRS. You might need these later for estate administration or if any questions come up. Also, since you mentioned she had Social Security income, be aware that if she received any Social Security payments after her date of death, those may need to be returned to the Social Security Administration. This is separate from the tax return but something to check on. The IRS has a helpful Publication 559 ("Survivors, Executors, and Administrators") that walks through all the requirements for filing a decedent's final return. It's available free on their website and really helped me understand the process when I was in your situation. You're doing the right thing by asking these questions and making sure everything is handled properly. Take it one step at a time.

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Sean Doyle

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Thank you for mentioning Publication 559 - that's such a valuable resource! I'm also dealing with a family member's final tax return and didn't know about this publication. Your point about Social Security payments received after death is really important too. I hadn't thought about that aspect. Do you know if there's a specific timeframe for returning those payments? And is it something the family needs to initiate, or does Social Security automatically detect it? Also, when you mention keeping detailed records for estate administration - are there any specific documents beyond the tax return copies that you found particularly important to keep? Sorry for all the questions, but this is all new to me and your experience sounds really helpful!

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