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Tyrone Hill
Quick thought - have you checked if your employers offer any tax preparation benefits? My company offers discounted tax prep through a partnership with H&R Block. Got my taxes done last year with multiple 1099s for only $350. Worth checking your benefits portal!
Harmony Love
ā¢I hadn't even thought of that! Great idea, I'll check with HR tomorrow. We do have a pretty decent benefits package at my main employer, so there might be something there. Thanks for the suggestion!
I was in a similar situation (married, home purchase, remote work) and ended up using a CPA for one year to learn the ropes, then did it myself after. Paid $850 in a HCOL area. The CPA taught me what to track throughout the year which made future filings much easier. My advice? Get more quotes, aim for someone in the $800-1000 range. Use them this year to set up a good system, then decide if you want to continue with them or DIY next year.
I did exactly this and it worked well. Had the CPA show me what documentation to keep for the home office deductions especially. Now I just use FreeTaxUSA and it's easy.
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Yara Assad
3 Something nobody's mentioned yet - have you considered a 1031 exchange? Instead of renting out your house, you could sell it and use the proceeds to buy a smaller residence for yourself PLUS another property to generate rental income. If done correctly, you can defer capital gains taxes.
Yara Assad
ā¢11 Wouldn't a 1031 exchange only work if both properties are investment properties? OP's house is currently their primary residence, so I don't think that would qualify.
Yara Assad
ā¢3 You're right, and that's an important distinction. For a 1031 exchange to work, the property must be held for investment or business purposes. In OP's case, they would need to convert their primary residence to a rental property first, rent it out for a period (usually at least a year), and then they could potentially use a 1031 exchange. Alternatively, OP could look into the primary residence exclusion, which allows you to exclude up to $250,000 ($500,000 for married couples) of capital gains when selling your primary residence if you've lived there for at least 2 of the last 5 years.
Yara Assad
2 Have you looked into the tax implications of converting your primary residence to a rental property? There are special considerations around the adjusted basis of the property for depreciation purposes.
Yara Assad
ā¢19 Yeah this is super important! When I converted my home to a rental last year, my accountant explained that the basis for depreciation becomes the LOWER of either your adjusted basis or the fair market value at the time of conversion. This made a big difference in my depreciation calculations.
Yara Assad
ā¢2 You're absolutely right. When converting a primary residence to a rental property, the depreciation basis is the lower of the adjusted basis (original cost plus improvements, minus any depreciation already taken) or the fair market value at the time of conversion. This is an important point because it affects how much depreciation can be claimed each year, which is a significant tax benefit of owning rental property. Also, don't forget that land isn't depreciable, so the basis needs to be allocated between the building (depreciable) and land (non-depreciable).
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Niko Ramsey
I work at a bank (not yours obviously) and we had a system update last year that accidentally flagged a bunch of domestic accounts as foreign. We had to send out 1042-S forms because the system had already generated them, but we made sure to zero out all the amounts so customers wouldn't be affected. Sounds like exactly what happened to you!
Is this kind of error common? Seems like a major screwup that could mess with people's taxes.
Jabari-Jo
Did anyone else notice OP said they received TWO copies of the 1042-S? That's actually normal - you're supposed to get multiple copies. One is for your records, one is for federal filing (though with $0 you don't need to file it), and sometimes a third copy for state filing depending on where you live.
Oh that makes sense! I thought they just sent me duplicates by mistake. So much about taxes is needlessly confusing lol.
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One thing nobody's mentioned yet is that you might want to consider claiming this as a non-business bad debt if you can't fully document it as a business bad debt. Non-business bad debts are treated as short-term capital losses, which isn't as good as an ordinary business loss, but still better than nothing. For it to qualify as a business bad debt, you generally need to show you were in the business of lending money or that the loan was somehow related to your trade or business. If it was just a one-off loan, the IRS might challenge a business bad debt classification. I went through this last year with a similar amount and ended up going the non-business bad debt route because it was less documentation and less risk of audit.
Interesting point! I actually made this loan with the intention of potentially becoming a partner in the business later, so there was a business motive beyond just earning interest. Would that help establish it as a business rather than personal loan?
That business connection definitely strengthens your case for treating it as a business bad debt. Keep any emails or documents that show discussions about partnership or business involvement. The key distinction the IRS looks for is whether you made the loan as an investment with business interests or simply as a personal loan. If you can document that connection to your own business activities or potential participation in their business, you're in a much better position to claim it as a business bad debt, which gives you the more favorable ordinary loss treatment rather than capital loss limitations.
StarSeeker
Don't forget the timing issue - the bad debt deduction must be taken in the year the debt actually becomes worthless, not when you decide to write it off. If you have evidence it became worthless in 2023, you should take it then. If it's becoming worthless in 2024, take it this year. Taking it in the wrong year is a common mistake and the IRS can disallow the deduction even if you have all the right documentation. Since you filed an extension for 2024 taxes (due Oct 2024), you need to determine if the worthlessness occurred in this tax year.
This is so important! My accountant told me the IRS is particularly picky about the timing of bad debt deductions. They expect you to take reasonable steps to collect before claiming worthlessness, but also don't want you waiting years after it's clearly uncollectible.
Sophie Hernandez
One simple thing that's helped me immensely is keeping a dedicated business credit card and ACTUALLY USING IT for all business expenses. I used to be lazy about this too, but now I force myself to use the right card even if it's inconvenient. Also, I take photos of all business receipts with notes using an app (I use Expensify but there are tons). This takes literally 10 seconds after a purchase and saves hours of frustration later. The app even extracts the merchant and amount automatically. For your trading activity, have you looked into specialized tax software for investors? I use TaxBit which integrates with most brokerages and automatically categorizes all trades for tax purposes.
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Daniela Rossi
ā¢Do you have any suggestions for handling situations where you forget and use the wrong card? This happens to me all the time and then I'm stuck trying to remember which purchases were actually business-related.
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Sophie Hernandez
ā¢When I accidentally use the wrong card, I immediately send myself an email with the details (what I bought, which card I used, and the business purpose). Then during my weekly review, I transfer those transactions to my business records. Another trick is setting different cards in different mobile wallets. I keep my business card as the default in Apple Pay and my personal as default in Google Pay. This creates a physical separation that helps me remember which is which.
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Ryan Kim
Honestly, the "clear answers" part of tax rules for small businesses and startups is a fantasy lol. Even CPAs disagree on some of the finer points! I used to stress about getting everything exactly right, but my accountant finally told me: "Document your reasoning, be consistent, and don't be ridiculous." Most tax issues aren't black and white - there's a whole lot of gray area. As long as you have a reasonable basis for your deductions and you're consistent in how you apply the rules, you're generally fine. The IRS is primarily concerned with people who are blatantly trying to cheat, not entrepreneurs who are making good-faith efforts to comply.
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Zoe Walker
ā¢This is so true. My dad was an accountant for 40 years and always said the same thing. He called it the "sleep at night" test - if your position is reasonable enough that you can sleep at night, you're probably fine. The tax code is too complex for perfect compliance.
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Ryan Kim
ā¢Exactly! And there's this misconception that an audit means you did something wrong. Sometimes it's just random selection. I've been through one, and it was basically just showing my documentation and explaining my reasoning. Since I had good records and wasn't trying to pull anything shady, it was pretty straightforward. The peace of mind comes from having a system, not from having perfect answers to every possible tax scenario. That's why I stopped obsessing over every little deduction and instead focus on consistent documentation.
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