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Ask the community...

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Nia Wilson

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One thing to keep in mind - the deadline for providing 1099-NEC to contractors is January 31, but you have until February 28 for paper filing to the IRS (March 31 if filing electronically). So you might still have time depending on when you're reading this. Also, don't forget you need the contractor's W-9 form before filing the 1099-NEC. If you don't have their correct TIN (tax ID number), you could face penalties for incorrect information.

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Omar Zaki

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Thanks for this clarification! The deadline thing was confusing me. I do have their W-9s collected already, so that part is covered at least. Do you know if there's any benefit to filing electronically versus paper, assuming I can get either done by the right deadline?

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Nia Wilson

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Filing electronically has several advantages over paper filing. First, you get that extra month (until March 31) to file with the IRS. Second, electronic filing significantly reduces the chance of errors since validation checks happen automatically. Third, you get immediate confirmation that your forms were received, unlike paper filing where you have no proof of receipt. Also, if you have to file 1099s for more than 10 contractors, you're required to file electronically anyway. Even with fewer forms, electronic filing is generally faster, more secure, and gives you better records for your business.

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Mateo Sanchez

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Another thing to consider - if you're using accounting software like QuickBooks, they usually have 1099 preparation built in. You can e-file directly through their system if you've been tracking your contractor payments correctly throughout the year. I've used this for the past 3 years and it's super simple - the system generates all the forms automatically based on how you've categorized payments. Worth checking if you're already using any accounting software!

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Aisha Mahmood

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Is this true for the cheaper versions of QuickBooks too? I have QB Self-Employed and wasn't sure if that includes 1099 filing or if it's only in the more expensive tiers.

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Aiden Chen

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When I started getting contractor income, my taxes got way more complicated. That "selecting" section might be about selecting if you had self-employment income. If you're using tax software, just answer honestly about having contractor income and it should guide you through the right sections. The most important thing is keeping good records of any business expenses. Even if you just drive for Uber on weekends or do some freelance work, track your miles, supplies, portion of phone bill, etc. These deductions can significantly reduce what you owe on that income.

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Zoey Bianchi

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Is there an easy way to track all this stuff for next year? I'm just starting some side gig work and tax season already seems daunting.

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just so you know, that contractor income means you'll probably owe more taxes than you're expecting. I made that mistake my first year - didn't set aside enough and got hit with a big bill. selfemployment tax is like 15% on top of regular income tax!! make sure to look into quarterly estimated payments for next year if you're continuing the contractor work. otherwise you might get hit with penalties too. wish someone had told me this my first time!

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Madison King

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Oh no, I had no idea about the extra tax! Do you think I'll owe a lot on $3,400 of contractor income? I'm already getting a small refund from my W-2 job so I was hoping that would cover any extra taxes.

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on $3,400 you're looking at around $480 just for self-employment tax (social security and medicare) before regular income tax. your refund might cover it, but it's definitely eating into what you would have gotten back. for next year, a good rule of thumb is to set aside about 25-30% of any contractor income for taxes. and yeah once you hit around $1000 in expected tax liability from self-employment, you're supposed to make quarterly payments to avoid underpayment penalties. it's a pain but better than a surprise bill!

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If your trust is really simple, I've used TurboTax Business for my family's trust for the past 3 years. It's not cheap (around $200) but still way less than an accountant. The interface is pretty easy if you have basic info like: - Trust's income sources (interest, dividends, etc) - Any expenses the trust paid - Info about distributions to beneficiaries Just make sure you have the right TurboTax version - the regular one won't do 1041s.

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Monique Byrd

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Thanks for the TurboTax suggestion. The $200 price tag is definitely more reasonable than $850! Is there a significant learning curve the first time you use it for trust returns? I'm trying to gauge how much time I should set aside to figure this out.

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The first year took me about 3 hours to get everything set up and understand how the trust taxation works. The software walks you through everything step by step, but there are some trust-specific concepts that take a bit to wrap your head around. The second and third years were much faster - maybe 45 minutes total since all the trust's basic information was already saved in the system. If your trust has straightforward income like interest or dividends, it's pretty manageable. The only tricky parts tend to be understanding when income is taxed at the trust level versus passed through to beneficiaries.

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Justin Trejo

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Gonna throw out a different suggestion - check if your local library has a VITA (Volunteer Income Tax Assistance) program. Some locations have volunteers certified to do basic trust returns, especially if the trust income is mainly from interest, dividends, or basic investments. Totally free service and might be worth checking into!

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Alana Willis

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VITA programs typically only handle basic 1040s with income under certain limits. I've never seen one that handles fiduciary returns like 1041s for trusts. Are you sure about this info?

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Benjamin Kim

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Former tax pro here. That quote is high but not outrageous given your situation and the Bay Area location. Here's what you can do: 1) Ask for an itemized breakdown of their services and associated costs. See if you can remove the review of past returns and consultations if you don't feel you need them. 2) Get at least 2 more quotes from other CPAs. Tax prep costs vary widely even within the same region. 3) Consider a tax pro who specializes in tech workers with RSUs - they'll be more efficient with your situation. For what it's worth, multi-state filing with RSUs at your income level is definitely complex and likely warrants professional help, but you should be able to find someone in the $2-3k range for just preparation of your current return.

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Zoe Wang

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Thanks for the insider perspective! If I do decide to just prep this year's return, can I still benefit from their expertise without paying for the full package? I'm worried that if I don't get the multi-year review, I might miss something important from previous years.

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Benjamin Kim

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You absolutely can benefit from their expertise on just this year's return. A good tax professional will naturally flag any concerning items they notice while preparing your current return, even without doing a formal review of previous years. If they spot something that looks like it might have been an issue in prior years, they'll mention it to you. Then you can decide whether it's worth paying for a more thorough review of those specific past returns. This more targeted approach often saves money while still addressing the most important issues.

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Have you considered a middle ground like H&R Block's premium service? They have CPAs and enrolled agents who handle complex returns with investment income and multi-state filing. Might cost around $500-800 which is way less than your quote but more thorough than basic TurboTax.

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I used H&R Block's premium service for a similar situation (RSUs and multiple states) and it was a disaster. They missed several deductions and didn't properly account for the double taxation issues between states. Had to file an amended return with a real CPA later. Would not recommend for truly complex situations.

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Questions about 1031 exchange with primary residence $250k exclusion - tax planning for future real estate moves

Hey everyone, I own my primary home outright and a rental property (multifamily) that still has a mortgage. I'm thinking about selling both eventually since I don't want to be a landlord forever and would prefer living closer to work. For the rental, let's say when I sell: value around $700k, original basis $450k, accumulated depreciation $100k, mortgage balance $275k, and selling costs $50k. After paying off the mortgage, I'd walk away with $375k cash. I'm considering using a 1031 exchange to buy a single-family rental at $650k with a 20% down investor loan ($130k), then renting it out for 2 years. Then I'd sell my current primary residence, take the $250k capital gains exclusion, and convert the rental into my primary residence. After living there for another 2 years, I might sell again. Let's assume the property would be worth $750k with $50k selling costs. My questions: 1. Would I qualify for the full $250k exclusion? I'd have $200k gain from the original 1031'd property and $50k from the new property. Would I only owe depreciation recapture at 25% federal plus state? 2. Can I refinance the investor loan to an owner-occupied loan after moving in? 3. Does the IRS care if I keep cash by increasing my loan size in a 1031? 4. Is the 1031 sale value calculated before or after selling fees? 5. If my replacement property costs less than what I sold, how do I calculate the taxes owed? 6. If instead I moved into one of the units in my current 4-unit multifamily for 2 years, would I get to exclude 25% of the gains ($50k in this case)? Realistically, I might stay in the final property until retirement (20+ years), but by then my gain would exceed the $250k threshold unless I get married for the $500k exemption. I'm also concerned about high real estate transaction costs, so I'd prefer minimizing the number of transactions unless the tax savings make it worthwhile. Thanks for any insight!

Sophia Carter

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One thing nobody's mentioned yet - the timing requirements for a 1031 exchange are super strict. You have 45 days to identify potential replacement properties and 180 days to close on the new property. If you miss either deadline, the whole exchange fails and becomes taxable. Also, you need to use a Qualified Intermediary to handle the funds - you can never touch the money yourself during the exchange or it becomes taxable. The QI will hold the proceeds from your sale and use them to purchase the replacement property. Given your multiple property strategy, you really need to map out the exact timing of each transaction to make sure everything qualifies as you expect.

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Chloe Zhang

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Do you have any recommendations for a good Qualified Intermediary? Also, can you partially do a 1031? Like if I sell for $700k but only want to reinvest $500k, can I just pay taxes on the $200k difference?

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Sophia Carter

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I've used IPX1031 for my exchanges and they were very professional, but there are many reputable QIs out there. I'd suggest asking your real estate agent or attorney for local recommendations since you'll want someone familiar with your state's requirements. Yes, you can absolutely do a partial 1031 exchange. If you sell for $700k and only reinvest $500k, you'd pay taxes on the $200k difference (called "boot" in 1031 terminology). Just be aware that the mortgage rules get a bit tricky - if your debt goes down too much in the exchange, that reduction in debt can also be considered boot. So if you had a $400k mortgage on the old property but only get a $200k mortgage on the new one, that $200k reduction in debt might be taxable as well.

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I went through almost this exact scenario last year. One thing to consider is that the "non-qualified use" rules have an important exception: periods where the property was used as a rental AFTER it was your primary residence don't count as "non-qualified use." But in your case, since you're going from rental→rental→primary, the gains from the original property would still be fully taxable when you eventually sell, regardless of how long you live there. The strategy that worked better for me was moving into my rental for 2 years FIRST, then doing the 1031 exchange from my new primary into another property that I then rented out. Different sequence, but much better tax outcome.

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Amaya Watson

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Thanks for sharing your experience! So if I understand correctly, it would be better tax-wise to: 1. Move into my current rental for 2+ years 2. Sell it as a primary residence (getting partial exclusion based on % of personal use) 3. Then do a 1031 on the taxable portion into a new rental property? That's an interesting approach I hadn't considered. Would definitely save on transaction costs too since I'd only be selling two properties instead of three in my original plan.

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Yes, that's exactly right! By moving into your rental first, you establish it as a primary residence. Then when you sell, you can take the $250k exclusion on the portion of appreciation allocated to your personal use (based on time). The remaining portion (from the rental period) would still be taxable, but that's where you can use the 1031 exchange to defer those taxes by rolling that portion into a new investment property. This approach is much cleaner tax-wise and as you noted, reduces your transaction costs significantly. Just make sure you keep very clear records of when the property usage changed and get a good appraisal at the time you convert it from rental to primary to establish the value at conversion.

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