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Why has nobody mentioned the potential for depreciation recapture? If you've been taking depreciation deductions on the commercial property (which you should have been), part of your gain will be subject to depreciation recapture at a rate of 25% rather than the lower capital gains rate. This can significantly impact your total tax bill.
Good point about depreciation recapture. Another issue is that if the S-corp distributes the proceeds from the sale to shareholders, it could potentially create additional tax issues depending on stock basis and AAA balance. The S-corp structure makes this way more complicated than if the property had been held in an LLC from the beginning.
Miguel raises an excellent point about depreciation recapture that could significantly impact your tax situation. If you've been claiming depreciation on the commercial property over the years (which you should have been doing), you'll need to "recapture" that depreciation when you sell. This recaptured depreciation is taxed at 25% rather than the more favorable long-term capital gains rates. Here's how it works: Let's say you've claimed $30k in depreciation over the years. When you sell, that $30k gets taxed at 25%, while the remaining gain ($145k in your case) would be taxed at capital gains rates. This can add a substantial amount to your tax bill that many people don't anticipate. You should pull your depreciation schedules from previous tax returns to calculate exactly how much you've claimed. If you haven't been taking depreciation deductions, you might want to consider filing amended returns to claim those deductions before selling - the IRS requires you to recapture depreciation whether you actually claimed it or not, so you might as well get the benefit of those deductions if you haven't already. This is another reason why getting professional help is crucial for S-corp property sales - there are multiple layers of taxation that can catch you off guard if you're not prepared.
One thing I haven't seen mentioned - if you're married filing jointly, you and your spouse can deduct up to $3,000 in capital losses against ordinary income. But if you're married filing separately, each of you can only deduct up to $1,500. Just a heads up in case anyone reading is considering changing filing status!
That's not accurate. The $3,000 limit ($1,500 if married filing separately) applies to the tax return, not per person. A married couple filing jointly still has the same $3,000 limit as a single filer. The $1,500 limit for married filing separately is because they're essentially splitting the $3,000 limit.
Just wanted to share my experience as someone who went through a similar situation last year. I had about $85,000 in capital loss carryovers from some poor crypto investments in 2022, and I was making the exact same mistake you were - only entering $3,000 instead of the full amount. The key thing to understand is that capital losses offset capital gains FIRST, and only then do you get to apply up to $3,000 against your ordinary income. So in your case, Oscar, you should definitely enter the full $120,000 carryover. Here's how it would work: 1. Your $30,000 crypto gains get completely wiped out by $30,000 of your carryover losses 2. You still have $90,000 in losses remaining 3. $3,000 of those remaining losses can reduce your ordinary income from your PT job 4. The final $87,000 carries forward to next year This is why TaxHawk is showing you a much better refund when you enter the full amount - you're eliminating all your capital gains tax liability. Don't second-guess the software on this one, it's handling the calculation correctly. Just make sure you keep good records of that $87,000 carryforward for next year's return!
Does anyone know if you can do a "catch-up" contribution to an HSA? I just realized I didn't max out my contribution for 2024 and I'm still doing my taxes now in 2025. Is it too late to put more money in and get the tax deduction?
Yes! You can make HSA contributions for the previous tax year until the tax filing deadline (usually April 15th). Just make sure you tell your HSA provider that the contribution is for tax year 2024, not 2025. I just did this exact thing last week!
Great thread! Just wanted to add another helpful tip for anyone dealing with HSA confusion - if you have both employer contributions AND personal contributions to your HSA, make sure you're tracking them correctly on Form 8889. I made the mistake last year of only reporting my personal contributions and forgot about the employer match that showed up on my W-2. The IRS sent me a letter asking about the discrepancy because the total on my 1099-SA didn't match what I reported. Had to file an amended return to fix it. Your W-2 will show employer HSA contributions in Box 12 with code "W" - make sure that amount plus your personal contributions equals the total contribution limit for your coverage type (individual vs family). The software should catch this if you enter everything correctly, but it's worth double-checking!
If you're using tax software like TurboTax or H&R Block, they usually have a section for "income reported to you incorrectly." You could potentially use that instead of Schedule C depending on your situation. Honestly though, the Schedule C route is probably cleanest since the IRS computer systems will be looking to match that 1099-NEC with something on your return.
I used TurboTax last year for something similar and it actually walked me through creating a Schedule C for this exact situation. Just make sure you select "business expenses" that match the categories of stuff you bought. It was pretty straightforward once I found the right section.
One thing I'd add is that you should double-check whether your volunteer work actually constitutes a "business" for Schedule C purposes. Since you were volunteering for a neighborhood watch group and not running a business, you might want to consider reporting this as "Other Income" on Form 1040 and then taking the expenses as miscellaneous deductions. However, given that you received a 1099-NEC (which is specifically for business income), the Schedule C approach mentioned by others is probably the safest route. The IRS matching system will expect to see that 1099-NEC amount reported somewhere on your return, and Schedule C is the most straightforward way to handle it. Just make sure when you fill out Schedule C that you clearly indicate this was volunteer reimbursement work, not a profit-seeking business activity. This can help if there are any questions later about your business activities.
Zainab Ismail
Another thing to check - make sure you're looking at the right numbers on TurboTax. Sometimes people look at the total tax WITHHELD (what came out of your paychecks) and mistake that for their expected refund. Your refund is just the difference between what you owed and what was already withheld. Double-check your TurboTax summary to make sure you're looking at the "refund" line and not something else.
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Amara Nnamani
ā¢I just double-checked my TurboTax summary and I was definitely looking at the refund amount. My federal refund was supposed to be $5,890 but I only got $3,381. Still waiting on the state portion. Guess I'll have to wait for that letter to find out what happened (if it ever gets forwarded to my new address).
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Rhett Bowman
Don't panic - this is actually pretty common! The $2,500+ difference between what TurboTax calculated and what you received suggests the IRS made adjustments to your return. Since this is your first time filing, there are a few likely culprits: 1. **Earned Income Tax Credit (EITC)** - If TurboTax calculated this credit but you didn't actually qualify based on your specific situation, the IRS would remove it 2. **Education credits** - These have strict eligibility requirements that software sometimes misses 3. **Filing status** - If there was any confusion about whether you can file as independent vs. dependent The good news is that you should receive a detailed notice (CP2000 or similar) explaining exactly what they changed and why. Since you moved, definitely contact USPS about mail forwarding ASAP, or create an online IRS account to access your records digitally. Your state refund will come separately - that part is totally normal. Each state processes at their own pace, so don't worry if it takes several more weeks. Focus on getting that IRS explanation letter first to understand the federal adjustment!
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