Do you think TurboTax's premier version would be sufficient for the following year, or would you recommend a different software?

TurboTax Premier would work fine for most people in this situation, but I personally prefer TaxSlayer or FreeTaxUSA. They handle all the same forms as TurboTax but cost significantly less. TurboTax charges premium prices for forms that the others include in their basic packages. The key is understanding which forms and schedules you need to complete. Once your CPA files this year, ask for a copy of your complete return and note which forms were used. Then verify that whatever software you choose next year supports all those forms. Most major tax software can handle multi-state returns, stock sales, and mortgage deductions - you just pay extra with some platforms.

Wow, I had no idea about the potential for double taxation on RSUs. My company did withhold some shares when they vested (about 22% I think), but I never fully understood how that affects my taxes when I sold them. This definitely makes me lean toward getting professional help this year. Do you know if this is something most CPAs understand well, or should I look for someone with specific experience in equity compensation?

Most CPAs should understand RSUs, but I would still specifically ask if they have experience with equity compensation when you're interviewing potential accountants. Some CPAs specialize in working with tech employees or others who receive significant stock compensation. When interviewing potential CPAs, ask them to explain how RSU taxation works. If they can clearly explain that RSUs are taxed as ordinary income when they vest (which should appear on your W-2) and then any additional gain or loss when sold is treated as capital gain/loss, that's a good sign they understand the basics. Make sure they can explain how to properly determine your cost basis, as that's where many people make mistakes. The right CPA can not only prepare this year's taxes correctly but also help you plan for future vesting and sales to minimize your tax burden.

Thanks for the advice! I do keep track of all my payments in a spreadsheet, but I was worried about what happens if my numbers don't match what's on the 1099s. Like what if I think a company paid me $7,500 but their 1099 says $8,000? Who is the IRS going to believe?

The IRS tends to go with what's reported on official tax documents like 1099s, but that doesn't mean you're stuck with incorrect information. If you receive a 1099 with an error, contact the issuer immediately and request a corrected form. They should issue a corrected 1099-NEC, which they'll also send to the IRS. If they refuse to correct it or you can't get it resolved before the filing deadline, you should still report your accurate income based on your records. On your tax return, you'd report the full amount shown on the incorrect 1099 to avoid automatic matching issues, but then make an adjustment to correct it. A tax professional can help you document this properly with your supporting evidence.

This happened to me too! Two of my biggest sponsorship deals were with companies that outsource their accounting, and somehow my address got messed up. Now I start emailing companies in December to verify they have my current info.

Did you have to pay back the tax benefits when you got audited? I'm worried about having to repay deductions years later plus penalties if something goes wrong.

I didn't have to pay back the deductions since the investment was structured legally, but I did have to pay for a specialized tax attorney ($8,500) to help defend the deductions during the audit. The IRS scrutinizes these investments closely. The bigger issue was that the project produced almost no oil after the first year, so my "investment" was basically worthless while the promoters walked away with their fees. The tax savings were real but not worth the stress and overall financial loss. If I had just invested that money normally and paid my taxes, I'd have been much better off. Don't let tax avoidance drive your investment decisions - it's usually a recipe for disaster.

I tried using TurboTax for my oil & gas partnership last year and it was a disaster. The software isn't designed to handle these specialized deductions properly. Had to hire an accountant anyway who told me I would have done it completely wrong. These investments require specialized tax knowledge - don't try to DIY it.

Can Cash App Taxes handle home office deductions for self-employed people? That's been the main reason I've stuck with the expensive options in the past.

Cash App Taxes definitely handles home office deductions for self-employed people. I used it last year for exactly that situation with my freelance work. The interface walks you through calculating the percentage of your home used for business and all the related expenses. The only limitation I found was if you're using the simplified home office deduction, it's straightforward, but if you're doing the regular method with depreciation and proportional expenses, you might want a more robust option if you're not familiar with the calculations. But for most typical home office situations, it works perfectly fine.

Is that actually legit? I always figured the free options would be bare-bones and missing features or have hidden fees at the end.

My job location didn't change, and I don't have health issues that required a move. As for "unforeseen circumstances" - is a new relationship considered unforeseen? It wasn't planned when I bought the house, but I doubt the IRS cares about that.

Unfortunately, a new relationship isn't considered an unforeseen circumstance by IRS standards. Their definition typically includes things like death, divorce that occurs DURING ownership, natural disasters, multiple births from the same pregnancy, or becoming eligible for unemployment. Since none of these apply, focusing on properly calculating your cost basis is your best strategy now. Make sure you include all purchasing costs, capital improvements, and selling costs to minimize the taxable gain. Document everything meticulously - the burden of proof is on you if you're audited.

This is good advice. I live in Colorado and discovered our state treatment of capital gains is different than federal. Saved me about $2,400 on my state return even though I still had to pay the federal capital gains.