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Has anyone else successfully charged between their own business entities like OP is considering? I'm in a somewhat similar situation with a consulting business and a rental property, and I sometimes do consulting work that benefits the rental. Never thought about actually charging between them.
I've been doing this for years with my photography business and vacation rental. I take professional photos of my rental for listings and I charge the rental business for this service. The key is documenting it properly and charging market rates. I've been through an audit once and they had no issues with this arrangement because I had proper documentation showing that I charge similar rates to other clients.
This is a really nuanced situation that requires careful handling. Based on what you've described, you're actually in a decent position to maintain business classification despite the recent losses. For your first question about the vacation rental paying your advertising business - this is absolutely legitimate as long as you treat it like any other business transaction. Create proper invoices, document the services provided, and charge fair market rates. This can actually help your Schedule C business show some income while providing a legitimate deduction for your rental property. Regarding the hobby classification concern - don't artificially inflate profits by not reporting expenses. Instead, focus on documenting your profit motive. Since you've had profits for most of the 20 years, that's strong evidence in your favor. Make sure you're documenting: - Your business plans and efforts to return to profitability - Marketing activities to drum up new clients - Any changes you've made to improve operations - Your expertise and time invested in the businesses The IRS looks at the totality of circumstances, not just recent losses. Your long history of profitability combined with documented efforts to improve the struggling business should support your business classification. The fact that you're actively trying to get new clients for the low-revenue business is particularly important to document. Consider keeping detailed records of your business development activities, client outreach efforts, and any strategic changes you're implementing. This demonstrates the businesslike manner and profit motive the IRS looks for.
This is really helpful advice! I'm curious about the documentation aspect - when you mention keeping detailed records of business development activities and client outreach, what format works best? Should these be formal business logs, or would something like email records and calendar entries showing client meetings/calls be sufficient? I'm trying to figure out the right level of documentation without going overboard.
Has anyone dealt with a situation where they rented out part of their house during the ownership period? I'm in a similar situation as OP but I rented out my basement for about 4 years of the 15 I've owned my house. Not sure how that affects the capital gains exclusion.
If you rented out part of your home, you'll need to allocate the gain between the residential and rental portions. The part that was used as rental is subject to depreciation recapture and might not fully qualify for the exclusion. I had to do this calculation last year - you basically determine what percentage of your home was rented (by square footage usually) and for what percentage of your ownership period.
Just wanted to add another important consideration for your situation with your son on the deed - make sure you understand the "lookback" rule if you're planning to sell in 2026. If your son was added to the deed for estate planning purposes but hasn't met the 2-year ownership requirement yet, you might want to time the sale strategically. For example, if he was added to the deed in early 2024, he'd meet the ownership test in early 2026. Combined with the use test (if he's been living there), this could make a significant difference in your tax liability. Also, since you mentioned you've lived there 18 years continuously, you definitely meet both tests for the full exclusion. Just make sure to keep good records of when your son was added to the deed and his residency status to properly calculate each person's eligibility when you file.
This is really helpful timing advice! I hadn't thought about strategically planning the sale date around the 2-year ownership requirement. Since estate planning often involves adding family members to deeds relatively recently, this could be a common issue for people in similar situations. Quick question - does the 2-year ownership requirement need to be exactly 2 full years, or is it 2 years out of the 5-year period before the sale? I want to make sure I understand the timing correctly for my own situation where I'm considering adding my daughter to my home's deed.
Pro tip: Start using your player's card! It's literally the easiest way to track your gambling. I resisted for years because I thought casinos would somehow use it against me, but now I always use it. At the end of the year, every casino will provide you with an annual win/loss statement if you used your card. It's official documentation that the IRS respects way more than personal notes. Most casinos let you request it online now.
Do player's cards actually track everything accurately though? I've heard they only track when you initially put money in and cash out, not all the ups and downs in between.
Player's cards are generally very accurate for tracking your net session results. They record your coin-in (total amount wagered) and coin-out (total amount paid out), which gives you your net win/loss for each session. This includes all the ups and downs - every spin, every payout, every bet. The casino's win/loss statement will show your net results by day, which is exactly what you need for tax purposes. It's way more reliable than trying to remember or manually track everything. Plus, if you're ever audited, having official casino documentation is much stronger than personal notes. Just make sure to insert your card before you start playing and don't forget to use it on every machine. Some people worry about privacy, but the IRS benefit far outweighs any concerns about the casino tracking your play.
One thing I learned the hard way is that you absolutely need to keep receipts for any cash you withdraw at the casino ATMs. Even if you don't use a player's card, those ATM receipts help establish a paper trail that shows you were actually gambling the amounts you're claiming as losses. Also, if you're serious about deducting gambling losses, consider opening a separate bank account just for your gambling activities. Transfer your gambling budget to that account, and only use that debit card at casinos. This creates a clear financial trail that's much easier to track and defend if the IRS ever questions your losses. The key is being able to show that the money you withdrew actually went to gambling, not other expenses. Having dedicated gambling funds makes this much clearer than trying to sort through your regular checking account transactions.
This is really smart advice about the separate gambling account! I wish I had thought of this earlier in the year. Do you recommend transferring a monthly gambling budget to this account, or just funding it before each casino trip? I'm trying to figure out the best way to set this up going forward so I have better records for next year's taxes.
I've been a retirement plan administrator for years and see this confusion all the time. When a 403(b) has both pre-tax and after-tax contributions, the rollover reporting can get messy. The distribution code "BG" is telling you something important. The "B" means qualified plan distribution, and the "G" specifically indicates this includes after-tax contributions. Those after-tax contributions ($12k in your case) should roll into your Roth IRA tax-free since you already paid tax on them. Only the earnings on those after-tax contributions (the $2k difference) would potentially be taxable when moving to a Roth. But if this was a direct transfer between trustees, even that might be reported differently. The blank in box 2a with unchecked box 2b is basically the provider saying "we don't know your tax situation, so we're not specifying the taxable amount.
That's super helpful, thanks! One thing I'm still confused about though - if the provider isn't specifying the taxable amount, how do I properly report this on my taxes? Is there a specific form or worksheet I need to use to calculate the taxable portion? I don't want to accidentally pay taxes on money that's already been taxed.
You'd report this on Form 8606, "Nondeductible IRAs." This form helps you track your basis (the after-tax contributions) to ensure you don't pay tax on it again. For the taxable portion (the earnings), you'd include that amount on line 4b of your Form 1040. Be sure to write "Rollover" next to line 4a to indicate this was a retirement account rollover. The difference between your gross distribution and the after-tax contributions ($2,000 in your case) would be the potentially taxable amount if you're converting to a Roth.
Has anyone used TurboTax to handle this kind of situation? I'm going through something similar and wondering if the software can handle these complex rollover situations correctly.
I used TurboTax last year for my 403(b) to Roth conversion and it handled it pretty well! The interview process asks specific questions about rollovers and walks you through entering all the information from your 1099-R forms. It specifically asked about pre-tax vs after-tax contributions and calculated the taxable portion correctly. Just make sure you have all your forms ready and enter the information exactly as it appears. TurboTax will prompt you about the distribution codes and ask if you rolled over to a qualified account. The software is actually pretty good at handling these retirement account scenarios.
Thanks for sharing your experience! That's reassuring to hear. I've got all my forms together, so I'll give it a try. Did you have to fill out Form 8606 separately or did TurboTax generate that for you automatically when you entered the information?
Dylan Baskin
I went through this exact same nightmare in early 2024! My refund got sent to an account I had closed months earlier and I was absolutely panicking about where my money went. The whole process took about 3 weeks from start to finish - bank rejected the deposit, SBTPG processed the return (which took forever), then mailed me a paper check. A few things I learned that might help you: - SBTPG's website updates are incredibly slow, so don't panic if the status doesn't change for days - Make sure your tax preparer confirms your current mailing address is on file with SBTPG - The paper check comes in the most generic envelope ever - seriously looks like junk mail, so be extra careful what you throw away - They'll deduct their processing fees before sending the check, so expect a bit less than your full $3,450 I know the waiting is torture when you need that money for bills, but it really does come through eventually. Their system is painfully slow but it works. Next year I'm definitely paying my prep fees upfront to skip this whole SBTPG middleman situation entirely - lesson learned the hard way!
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Chloe Harris
ā¢This is really reassuring to hear! I'm going through the exact same thing right now and the uncertainty is driving me crazy. Three weeks feels like forever when you're waiting for money you desperately need, but it's good to know there's actually a predictable timeline. I've already been checking the SBTPG site obsessively and you're absolutely right - their updates are painfully slow. Thanks for the heads up about the generic envelope too - I definitely would have tossed that thinking it was spam! Definitely learned my lesson about paying prep fees upfront next year to avoid this whole mess.
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Bruno Simmons
I'm actually going through this exact situation right now too! My refund got sent to an account I closed back in December and I just found out yesterday. Reading through all these comments has been really helpful - sounds like the 2-3 week timeline is pretty consistent across everyone's experiences. The most frustrating part is how SBTPG makes it nearly impossible to get any real information about what's happening. Their website barely updates and from what everyone's saying, calling them is basically useless unless you want to spend your entire day on hold. I've already double-checked that my tax preparer has my current address on file, and after reading all these warnings about the plain envelope, I'm going to be super paranoid about checking every piece of mail that comes in over the next few weeks. Definitely don't want to accidentally throw away my own refund! This whole experience has convinced me to pay my prep fees upfront next year to avoid the SBTPG middleman entirely. Seems like such an obvious way to prevent this headache. Thanks everyone for sharing your timelines and tips - makes me feel a lot less anxious knowing this actually does get resolved eventually, even if the system is painfully slow.
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Ravi Patel
ā¢Welcome to the "closed bank account refund limbo" club! š It's frustrating that so many of us are dealing with this same issue. The good news is that based on everyone's experiences here, the 2-3 week timeline seems pretty reliable even though it feels like forever when you're waiting. I'm impressed you already thought to double-check your address with your tax preparer - that's smart thinking. The envelope warning from everyone is definitely worth taking seriously too. Hang in there, sounds like we'll both be getting our checks soon enough!
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