Does anyone know if wash sale rules apply to crypto trading? I've been doing some active trading this year on Coinbase and Binance and I'm not sure if I need to track wash sales the same way as with stocks.

Great question about handling brokerage fees! I went through this exact same confusion when I first started tracking my cost basis properly. Just to reinforce what Max mentioned - you're absolutely right that purchase fees get added to your cost basis ($135 + $12.50 = $147.50), but selling fees come off your proceeds instead of being added to cost basis. One thing I learned the hard way is to make sure you're tracking ALL fees, not just the obvious commission charges. Some brokers have regulatory fees, exchange fees, or other small charges that can add up over time. These all follow the same rule - purchase-related fees increase your basis, sale-related fees reduce your proceeds. Also, if you're doing more active trading now, definitely keep detailed records throughout the year rather than trying to reconstruct everything at tax time. Your broker's 1099-B should show the fees, but it's good to have your own records as backup, especially if you're trading across multiple platforms. The IRS is pretty clear on this treatment in Publication 550 if you want to read the official guidance, but the way Max explained it is spot on for your situation.

Just wanted to add something I learned the hard way - if you're financing the car, make sure you understand how the lender handles the sales tax payment. When I bought my car last year, I assumed the loan amount would cover the vehicle price plus tax, but my lender only financed the car's value and I had to pay the sales tax separately at signing. This was a $1,400 surprise I wasn't prepared for! Some lenders will include tax in the loan, others won't. Ask your financing source upfront whether sales tax is included in your loan amount or if you need to bring a separate check/payment for taxes and fees on the day you pick up the car. Also worth mentioning - if you're getting financing through the dealer, they'll often roll the tax into your loan automatically, but if you're using your own bank or credit union, double-check this detail to avoid any last-minute scrambling for cash.

As someone who works with tax regulations daily, I want to emphasize a crucial point that might save you money: always verify the exact tax rate for your specific county in Nevada before making your final decision. Nevada's sales tax varies significantly by county - ranging from around 6.85% to over 8.25% depending on local taxes and special districts. For example, if you're in Clark County (Las Vegas area), you'll pay a different rate than someone in Washoe County (Reno area). This difference can be $200-300 on an $18,000 purchase, which might change whether buying in California actually saves you money after factoring in travel costs. Also, don't forget about Nevada's Governmental Services Tax (GST) that gets added to vehicle registrations - it's a flat fee that varies by vehicle value and isn't always clearly disclosed upfront. The DMV website has a fee calculator, but as others mentioned, calling ahead or using one of those tax calculation tools can help you get the complete picture before you commit to either purchase location.

I went through this exact situation about 6 months ago when I needed to file 2021 and 2022 returns. The key thing to understand is that you need "Wage and Income Transcripts" specifically - not just regular tax return transcripts. These show all the income that was reported to the IRS under your SSN for those years. Here's what worked for me: I called the IRS transcript line at 800-908-9946 early in the morning (around 7 AM) and was able to get through after about 45 minutes on hold. When I explained I needed unmasked transcripts for filing back taxes, they mailed them to my address on file within about 2 weeks. One important tip - when you call, specifically ask for "unmasked Wage and Income Transcripts" for tax years 2022 and 2023. Don't just say "transcripts" because they might send you the wrong type or the masked versions that won't help with filing. Also, while you're waiting for the transcripts, you can start gathering any other tax documents you might have - bank statements showing interest earned, receipts for deductible expenses, etc. The transcripts will show your reported income, but you'll still need documentation for deductions and credits. Good luck! Filing back taxes is stressful but getting those unmasked transcripts is definitely the right first step.

I went through this exact same situation last year and it was such a headache at first! The terminology is definitely confusing - "unredacted" and "unmasked" mean the same thing in this context. You need transcripts that show all the details without any information blocked out for security purposes. Here's what I learned: The fastest way is actually to visit an IRS Taxpayer Assistance Center if you have one nearby. You can schedule an appointment online at irs.gov/help/contact-your-local-irs-office, and they'll print your unmasked Wage and Income Transcripts right there during your visit. This saved me weeks compared to waiting for mail delivery. If you can't get to an office, calling 800-908-9946 early in the morning (like 7 AM Eastern) gives you the best chance of getting through. Just be prepared to wait on hold and have your SSN and previous tax info ready for identity verification. One thing to keep in mind - these transcripts will show all income reported to the IRS under your SSN, but they won't have information about deductions you might be eligible for. So while they're perfect for ensuring you report all your income accurately, you might still want to work with a tax professional to make sure you're not missing out on deductions that could reduce what you owe for those back years. The penalties do add up over time, so getting this sorted sooner rather than later is definitely the right move. Good luck!

This has been such a comprehensive discussion! I'm also an S-corp owner dealing with health insurance deductions, and I wanted to add one point that might be helpful for others in similar situations. Regarding the concern about your wife's employer not offering health benefits - since her school district doesn't provide coverage options, this shouldn't create any eligibility issues for your self-employed health insurance deduction. The IRS limitation only applies when affordable employer coverage is actually available, not when an employer simply exists without offering benefits. I've been through a similar setup process with my accountant, and one thing that streamlined everything was creating a simple spreadsheet tracking all premium payments throughout the year. This made the quarterly reimbursement requests much easier to process and gave us bulletproof documentation for tax purposes. Also, don't forget that once you have the proper S-corp reimbursement structure in place, you might want to explore other health-related benefits like HSA contributions if you switch to a high-deductible health plan in the future. The formal reimbursement plan can often be expanded to cover additional health benefits. The consensus seems clear - with $16,300 in combined premiums and your profitable business, you're looking at substantial tax savings that will far exceed any setup costs. Getting this structured properly before year-end should be a priority!

Excellent question about quarterly estimated taxes! When you set up the S-corp health insurance reimbursement system, you're essentially creating a tax-neutral transaction - the reimbursements increase your W-2 wages (subject to income tax) but you get an offsetting deduction on your personal return. However, there's a timing consideration for estimated taxes. Your quarterly withholdings will increase slightly because the health insurance reimbursements are subject to income tax withholding through payroll, but you won't get the benefit of the offsetting deduction until you file your annual return. In practice, this usually doesn't require major adjustments to your estimated payments because the net tax effect is minimal - you're mainly shifting the timing of when you get the tax benefit. The bigger advantage is the AGI reduction, which can help with other income-based limitations and phase-outs. If you're converting from sole proprietorship to S-corp, definitely factor in the health insurance benefits when doing your cost-benefit analysis. Between the potential FICA tax savings on business profits and the improved health insurance deduction structure, it can be quite compelling for profitable businesses. Just make sure to work with an experienced CPA who understands S-corp compliance requirements!

Just to add another perspective - I made this exact mistake my first year filing taxes! I was using my net income from my final paystub because I thought that was my "actual" income. Ended up having to amend my return when I realized the error. The key thing that helped me understand it: your paystub shows net pay because that's what you take home, but the government needs to know your total earnings (gross) to calculate what you should owe in taxes. The taxes already taken out of your paycheck are just prepayments - like making installments on a bill. So definitely use your W-2 Box 1 for wages, and don't overthink it. The form is designed to walk you through the process step by step once you have the right starting numbers.

This thread has been super helpful! I'm a newcomer to filing taxes myself (my parents used to handle everything), and I was making the same mistake of looking at my net pay and trying to figure out how that related to my taxes. Reading through all these explanations, especially about how pre-tax deductions work and why Box 1 on the W-2 is the number that matters, really cleared things up for me. I had no idea that my 401k contributions were already reducing my taxable wages before they even got to my tax return. One question though - if I have both a regular job with a W-2 AND did some freelance work with a 1099, do I still start with my W-2 Box 1 amount and then add the 1099 income on top of that? Or is there a different process when you have mixed income types?