Great question! You're absolutely right that a roof replacement should be depreciated over 39 years, not 15. The qualified improvement property (QIP) designation specifically requires interior improvements to nonresidential buildings, and a roof is clearly exterior. However, I'd recommend looking closely at your project details. If you replaced any skylights, those might qualify for different treatment since they could be considered separate from the roof structure. Also, any insulation upgrades or ventilation improvements might be separable components with their own depreciation schedules. Since you can't use Section 179 this year due to income limitations, make sure you understand that this is an annual election. If your income situation improves in future years, you might be able to elect Section 179 for other qualifying property purchases. One more thought - if this roof replacement was due to storm damage or other casualty, there might be additional considerations for how to handle the tax treatment. But for a standard replacement, you're stuck with the 39-year schedule for the actual roofing components.

I've been following this discussion and wanted to add some clarity on the depreciation question. You're absolutely correct that the roof itself should be depreciated over 39 years as building property, not 15 years as QIP. However, I'd strongly encourage you to review your project invoices more carefully. Even though the overall project is a "roof replacement," there are often components that can legitimately be separated and depreciated under different schedules. For example: - Any new electrical work (lighting, outlets, panels) - typically 7-year property - HVAC equipment or ductwork modifications - usually 5-year property - Security systems or cameras installed during the project - 5-year property - Interior work done to access the roof (drywall repair, paint) - potentially QIP if it's interior improvements The key is having proper documentation. Your contractor should be able to provide a detailed breakdown showing labor and materials for each trade. This isn't about gaming the system - it's about properly classifying legitimate separate assets that happen to be part of a larger project. Given the $87k total cost, even identifying $15-20k worth of components with shorter depreciation lives could provide meaningful tax savings compared to treating everything as 39-year property. Also, don't forget that Section 179 elections can be carried forward to future years when your income situation improves, so keep that option in mind for next year's planning.

This thread has been incredibly comprehensive and helpful! As someone who's been dealing with a similar social casino tax situation, I wanted to share one additional perspective that might help with your decision. The systematic approach everyone has outlined is spot-on - getting those detailed CSV transaction histories from the platforms is absolutely the first step. What I found surprising was how willing the customer service teams were to provide comprehensive records when I mentioned it was for tax purposes. They clearly deal with these requests regularly. One thing that really helped me feel confident about the documentation was creating a simple summary spreadsheet that reconciled the platform CSV data with my bank statements. This showed a clear money trail and made it easy to calculate net gambling losses. Having that reconciliation made me feel much more prepared in case of any IRS questions. For your $33k in withdrawals, if you're like most social casino players and deposited more than you withdrew, the potential gambling losses could be substantial. Combined with mortgage interest and other typical itemized deductions, you could be looking at meaningful tax savings - several people here saved $1,400-$2,800 by taking this approach. The documentation requirements really aren't as scary as they initially seem. Platform CSV files + bank statements + withdrawal confirmations appears to be adequate for most situations. Much more manageable than trying to reconstruct detailed session logs from memory. Whatever you decide, you're being smart to think it through carefully and report the income properly. Good luck with whichever approach you choose!

After reading through all these detailed responses, I'm convinced you should definitely follow the systematic approach everyone has outlined. The potential tax savings with $33k in withdrawals could be substantial if you have significant gambling losses to offset those winnings. Here's what I'd recommend based on everyone's experiences: First, immediately contact both Modo and Crown Coins customer service to request complete transaction histories in CSV format for 2024. Be upfront that it's for tax purposes - they're used to these requests and will provide comprehensive records including dates, transaction types, amounts, and reference numbers. Once you have those detailed records, calculate your total deposits versus your $33k in withdrawals. If you're like most players and deposited more than you withdrew, those gambling losses could be significant. Then add up all your other potential itemized deductions (mortgage interest, state/local taxes, charitable contributions) and compare to the standard deduction. Multiple people here saved $1,400-$2,800 by taking this approach, and the documentation requirements are much more manageable than initially feared. The CSV files from platforms combined with your bank statements and withdrawal confirmations provide adequate records for the IRS - you don't need detailed daily gambling logs. Even if you ultimately decide the standard deduction is better for your situation, at least you'll know you made an informed choice based on actual numbers rather than assumptions. Either way, definitely report the full $33k as gambling income on Schedule 1 - that part isn't optional regardless of which deduction method you choose. Good luck with whatever approach you decide on - you're being smart to think this through carefully!

Just to clarify, Form 5329 has multiple parts and isn't just for early distributions. It's also used for excess contributions to IRAs, excess accumulations (not taking RMDs), etc. So depending on your situation, you might need different parts filled out.

I ran into this exact same issue with Credit Karma Tax last year! The software can be really finicky about generating Form 5329. A few things that helped me get it to work: 1. Make sure you answered "Yes" when it asks if you received any retirement plan distributions 2. Double-check that you entered the correct distribution code from your 1099-R (should be code 1 for early distribution) 3. When it asks about the reason for the distribution, be very specific - don't just say "personal use" if that's what happened The form IS required for any early distribution, regardless of whether you qualify for an exception. If you do qualify for an exception, that's where you'd claim it on the form to avoid the 10% penalty. If Credit Karma still won't cooperate, you can always download Form 5329 directly from the IRS website and fill it out manually. Just make sure to include it with your return and transfer the additional tax amount to line 17 of your Form 1040. Sometimes the manual approach is actually easier than fighting with buggy software!

Does anyone know how this Box 6 issue works with tax software like TurboTax? When I enter my 1099-NEC info, it seems to automatically assign the income to the state listed in Box 6, but that's not where I live or work.

This is such a helpful thread! I'm dealing with a similar situation where I live in Oregon but work remotely for a company in New York. My 1099-NEC has New York listed in Box 6, but I've never even been to New York - all my work is done from my home office in Oregon. From what I'm reading here, it sounds like I should report this income to Oregon since that's where I physically performed the work, regardless of what Box 6 says. But I'm worried about getting audited if I don't follow what's printed on the form. Has anyone had experience with state audits over this kind of discrepancy? Should I reach out to my client to get a corrected 1099-NEC, or is it safe to just allocate the income to Oregon when I file?

Just want to add my experience - I was in an almost identical situation last year. Had 3 years of unfiled taxes with both W-2 and 1099 income. I decided to DIY with tax software and regret it now. I thought I was saving money, but I missed several deductions that would have saved me thousands. I also messed up the estimated tax penalty calculations which caused more issues. Then I tried amending the returns myself which created an even bigger mess! Finally hired a tax pro who had to fix everything. Cost me way more in the end than if I'd just hired them at the beginning. Just my 2 cents, sometimes trying to save money costs more in the long run.

I want to share some practical advice from someone who went through a very similar situation recently. First, don't panic - this is absolutely manageable even though it feels overwhelming right now. For your unfiled returns (2015, 2018, 2020), the most important thing is getting them filed ASAP to stop the failure-to-file penalties from growing. These penalties are typically much higher than failure-to-pay penalties. Since you mentioned your returns are relatively straightforward, you could potentially handle the preparation yourself using prior year tax software. However, given that you have over $20k in total tax debt between your back taxes and unpaid 2023 estimated payments, I'd lean toward getting professional help for a few key reasons: 1. **Penalty abatement opportunities** - A tax pro can often get first-time penalty abatements or reasonable cause waivers that could save you hundreds or thousands 2. **Maximizing deductions** - Even "simple" 1099 work often has more deductible expenses than people realize (home office, mileage, equipment, etc.) 3. **Payment plan strategy** - They know how to structure installment agreements to get the best terms and can handle both your back taxes and 2023 shortfall in one comprehensive plan The $450 per year might seem expensive, but if they can reduce your tax liability by even 10-15% through proper deductions and penalty abatement, that fee pays for itself many times over. Plus, having everything handled correctly the first time prevents costly amendments later. For immediate next steps: gather all your tax documents for those years, and consider getting quotes from a few different tax professionals who specialize in tax resolution, not just basic tax prep.