I'd also recommend checking out the IRS Volunteer Income Tax Assistance (VITA) program if you're looking for free help with your taxes. Since you mentioned you're not a tax expert, VITA volunteers can help you prepare and file your return for free if your income is under $64,000. They're trained to handle W2s and various 1099 forms. You can find VITA sites at libraries, community centers, and other locations using the IRS VITA site locator. It's especially helpful if you want someone to walk through your tax situation with you in person rather than trying to navigate software on your own. The volunteers are IRS-certified and can handle most individual tax situations including multiple income sources like yours.

Thanks everyone for all the great suggestions! I'm definitely going to try a few of these options. The automatic document scanning feature that @Ethan Clark mentioned with taxr.ai sounds really appealing since I hate manually entering all those 1099 boxes - I always worry I'm going to mess something up. I'm also intrigued by the VITA program @Emma Johnson suggested. I didn't know that was a thing! Having someone walk through everything with me in person might be worth it for peace of mind, especially since this is my first year dealing with multiple 1099s. Quick question for anyone who's used these services - do any of them handle estimated tax payments for next year? Since I'll probably have similar 1099 income next year, I want to make sure I don't get hit with underpayment penalties.

Girl don't stress too much! I've been through this exact same thing before and TT152 disappearing is usually actually a GOOD sign that your return is moving through the system. The generic "still being processed" message is super annoying but it doesn't mean anything bad necessarily. Since you filed 1/17 and got accepted 1/21, you're right in that normal processing timeframe. I'd give it maybe another week or two before calling - the phone lines are absolutely insane right now anyway. Try to check your transcripts if you can access them, that'll give you way more info than WMR! Hang in there bestie, your refund is probably coming soon! 💪

Hey! I totally get the anxiety - I was in the exact same situation last month and it drove me absolutely nuts checking WMR constantly 😅 The disappearing TT152 actually ended up being a good sign for me - got my DDD like 4 days later! The generic "still processing" message is super frustrating but try not to read too much into it. Your timeline sounds totally normal for this time of year. The IRS is swamped right now so delays are pretty common. I'd definitely try checking your account transcripts on irs.gov if you can - they update faster than WMR and give you way more detailed info about what's actually happening with your return. Hang tight, you're probably closer than you think! 🤞

Quick question - does anyone know if you can pay yourself partially as a 1099 contractor and partially through distributions? One of the CPAs I talked to suggested this approach but it seems weird to be both an employee AND a contractor for my own S-Corp.

This is exactly the kind of confusion that drives S-Corp owners crazy! Here's what I've learned after going through this same struggle: the "reasonable compensation" requirement is real and non-negotiable, but there's definitely room to optimize within the rules. With $270k in business income and comparable positions at $133k, I'd lean toward taking somewhere between $100k-$120k as W-2 salary. That CPA suggesting $60k might be too aggressive given your income level and industry standards. Remember, the IRS looks at the total picture - if you're taking $210k in distributions but only $60k in salary, that ratio could trigger scrutiny. The key is documentation. Keep records of salary surveys in your field, job postings for similar roles, and any other evidence that supports your compensation level. I also recommend having your CPA prepare a memo explaining the reasoning behind your salary/distribution split in case you ever need to defend it. One thing to consider: while minimizing payroll taxes saves money now, those reduced Social Security credits will impact your future benefits. It's a trade-off worth factoring into your decision.

Has anyone actually gone through an audit after doing one of these F Reorganizations for an S-Corp sale? I'm curious how aggressively the IRS reviews these structures given that they seem to give buyers tax benefits without the seller paying corresponding higher taxes.

Noah, I just went through something very similar with my software consulting S-Corp earlier this year. The PE firm also insisted on the F Reorganization structure, and I was initially nervous about the complexity. Here's what I learned: the F Reorg can actually be quite favorable for sellers when done correctly. You're essentially getting the best of both worlds - capital gains treatment for yourself while giving the buyer their desired asset purchase benefits. A few key points from my experience: - Make sure your tax attorney specializes in these transactions. The sequencing is critical and small mistakes can blow up the entire tax benefit. - The $3.2M sale price should qualify nicely for long-term capital gains treatment (assuming you've held the stock for over a year). - Budget for higher legal fees upfront - I spent about $15K on tax attorneys but it saved me over $250K in taxes compared to an asset sale. One thing to watch: if you have any debt forgiveness or seller financing components, make sure those are structured properly to maintain capital gains treatment. Also, any Section 1202 qualified small business stock benefits you might have should be preserved through the reorganization. The structure is legitimate and well-established - don't let the complexity scare you away from what could be significant tax savings. Just make sure you have the right professionals guiding you through it.

Just a heads up that the IRS is currently giving extra scrutiny to Schedule F (farm income) returns that show significant losses against W-2 income. My buddy got audited last year for exactly what you're describing - he had about $200k in W-2 income and tried to write off $25k in farm equipment for his new 12-acre property. The key factor that triggered the audit was insufficient revenue from actual farm operations. They disallowed most of his deductions as "hobby farm" expenses. If you're serious about making this work, make sure you're generating some legitimate farm income ASAP.

Your tax guy is correct about long-term agricultural investments, but there are some important nuances to understand. The IRS does recognize that certain farming operations like orchards, vineyards, and timber have extended establishment periods before generating income. However, you still need to demonstrate legitimate business intent and follow proper procedures. For tree crops, you'll want to establish a formal business plan showing projected income timelines, maintain detailed records of all expenses, and ideally generate some interim revenue (even small amounts from selling seedlings, offering consulting, or agritourism activities). The key is showing you're actively engaged in farming activities, not just planting trees and waiting. Consider starting with some shorter-term crops alongside your tree investments - vegetables, herbs, or cut flowers can provide immediate income while your long-term investments mature. This helps establish the business legitimacy that protects your deductions during the establishment years. Also document everything related to your farming education - workshops, extension courses, agricultural publications. This helps demonstrate expertise and business intent if questioned.