This is a great comprehensive discussion! One additional consideration that might help with your planning - have you looked into the timing of when you dispose of the old truck versus when you place the new one in service? If you can manage to dispose of the old truck late in the year and place the new truck in service early the following year, you might be able to spread the recapture income and new depreciation across two tax years. This could help with cash flow and potentially keep you in lower tax brackets if your business income varies year to year. Also, since you're in construction, make sure you're considering the half-year convention rules. If you placed the old truck in service in the second half of 2023, you might have additional depreciation opportunities that could affect your recapture calculation. The QBI impact mentioned by @Chloe Green is really important too - that asymmetry between recapture not being QBI eligible while new depreciation reduces QBI can add up to real money over time.

I'm dealing with a similar vehicle trade-in situation and this thread has been incredibly helpful! One aspect I'm still unclear on though - when you report the depreciation recapture on Form 4797, does it get treated as self-employment income subject to the 15.3% SE tax, or just ordinary income tax rates? Given that Isabella's looking at $74,360 in recapture, that SE tax distinction could mean an additional $11,000+ in taxes beyond the regular income tax. I know regular depreciation deductions reduce SE income, but I'm not sure if the recapture flows through the same way when you dispose of the asset. Also, for future planning - has anyone considered the new 100% bonus depreciation phase-out that starts in 2023? The rates drop to 80% in 2023, 60% in 2024, 40% in 2025, 20% in 2026, and then zero after that. This might affect the timing of when to make major equipment purchases if you're trying to minimize the recapture cycle that several people mentioned.

Does anybody know if buying snacks for the team after games counts as a deductible expense? I probably spent like $400 last season on post-game treats for my volleyball team.

Great thread everyone! As someone who's coached youth tennis for 6 years, I want to emphasize the importance of keeping detailed records from day one. I learned this the hard way when the IRS questioned my deductions in year 3. A few additional tips from my experience: - Take photos of equipment you buy for the team (with receipts) showing it stays with the organization - Keep a simple log of volunteer hours even though you can't deduct time - it helps establish the scope of your volunteer commitment - If you travel to away tournaments, overnight travel expenses (hotels, meals) can also be deductible if the trip is primarily for volunteer purposes - Don't forget about uniforms or coaching gear you purchase that has the team/organization logo - these are clearly for volunteer use only The 14 cents per mile adds up fast when you're driving to multiple practices and games per week. Last year I deducted over $600 in mileage alone, plus another $300 in equipment and supplies. Just make sure your youth organization is actually a registered 501(c)(3) - you can verify this on the IRS website or ask them for their determination letter. Keep volunteering and helping these kids - the tax benefits are just a nice bonus for the great work you're already doing!

Has anyone actually had their OIC accepted when they couldn't provide spouse info? My tax guy told me they almost always reject these applications if you're missing any info they ask for.

I went through something very similar about 2 years ago - owed $28k and had been separated for 6 years but never officially divorced. My ex also refused to provide any financial information or cooperate at all. Here's what worked for me: I gathered every piece of documentation I could find to prove we were living completely separate lives. This included different addresses on utility bills, separate car insurance policies, different phone plans, bank statements showing no shared accounts, and even testimony from neighbors who could confirm we hadn't lived together in years. The most important thing was being completely honest and transparent with the IRS. I submitted a detailed written statement explaining the entire situation, including my attempts to contact my ex (I kept screenshots of unanswered texts and emails). I also included an affidavit stating that to the best of my knowledge, she had minimal income, but that I had no way to verify this. My OIC was initially put on hold for additional review, but after about 4 months, it was accepted at about 25% of what I owed. The key was showing that I made every reasonable effort to get the information but couldn't due to circumstances beyond my control. Don't give up - the IRS does have procedures for situations exactly like yours. Just make sure you document everything and be completely truthful about your attempts to get her cooperation.

I went through something very similar last year and ended up with FreeTaxUSA after comparing it with TurboTax and H&R Block. The filing status confusion is super common - I had myself listed as Single in one program and Head of Household in another without realizing it. One thing that really helped me was calling the IRS's automated phone line (1-800-829-1040) and using their Interactive Tax Assistant tool online to confirm my filing status before finalizing anything. Since you're a single parent, Head of Household is almost certainly correct if your child lived with you for more than half the year. For the state return differences, I found that FreeTaxUSA sometimes picks up on local tax credits that the bigger software companies miss or calculate differently. That $78 difference might actually be in your favor! I'd trust the software that asks more detailed questions about your specific situation. The $100 savings with FreeTaxUSA is definitely worth it if you've got the federal numbers matching now. Just make sure to use their review feature before filing - it's pretty thorough at catching any remaining discrepancies.

I've been through this exact same frustration! The standard deduction discrepancy you're seeing is almost certainly due to filing status differences between the programs. Since TurboTax and TaxAct both show $20,800, that's the Head of Household standard deduction for 2023, while FreeTaxUSA's $13,850 is the Single filer amount. As a single parent, Head of Household is likely the correct status for you if your child lived with you for more than half the year and you paid more than half the household expenses. Double-check this setting in FreeTaxUSA - it's easy to miss during initial setup. For the state return differences, don't stress too much if it's only $78 off now. State calculations can vary between software due to how they handle local taxes, credits, and deductions. FreeTaxUSA often asks more detailed location-specific questions, which might actually make their calculation more accurate. Given that your federal returns now match and you're saving $100, I'd say go with FreeTaxUSA. Just make sure to use their final review feature before filing - it's pretty good at catching any remaining issues. The interface might be clunkier, but the savings are worth it for straightforward returns like yours.

I learned the hard way about the passive activity loss rules and depreciation. Make sure you're keeping detailed records of disallowed losses! When I sold my rental last year, I couldn't find my records showing which depreciation had been disallowed vs. allowed. The IRS assumed ALL scheduled depreciation had been taken, even though some was disallowed. Had to hire a tax pro to reconstruct 7 years of depreciation schedules and passive loss worksheets. Cost me $1,200 just for that service. Could have avoided it with better record keeping.

Great question about tracking disallowed depreciation! I've been using TaxAct for my rental properties and it has a pretty decent depreciation worksheet that carries forward the disallowed amounts from year to year. It shows both the calculated depreciation and what was actually allowed each year. But honestly, I also keep a separate Excel spreadsheet as backup. I track: (1) the full MACRS depreciation amount, (2) business use percentage each year, (3) calculated depreciation after business use adjustment, (4) amount actually allowed after passive loss rules, and (5) cumulative disallowed amounts carried forward. The key is making sure your tax software and your manual tracking agree each year. When you eventually sell, you'll need to prove which depreciation was actually taken vs. just calculated. The IRS doesn't care that your software "calculated" depreciation if the passive loss rules prevented you from actually taking it. Also recommend printing or saving PDFs of your depreciation schedules and Form 8582 (passive loss worksheet) each year. Digital files can get corrupted or lost, but you'll definitely need this documentation later!