Has anyone used TurboTax Self-Employed for this situation? I'm also a teacher with some side consulting work, and wondering if it's worth paying for that version vs just the regular one.

As someone who went through this exact transition from teacher-only income to teacher + 1099 freelance work, I can't stress enough how important it is to get organized NOW rather than waiting until tax season. The quarterly payment approach is definitely the safest route, but increasing your W-4 withholding at school is much more convenient if you can swing it. I'd recommend calculating about 25-30% of your expected freelance income and having that withheld from your teaching paychecks over the remaining pay periods. Don't forget to open a separate business checking account for your freelance income and expenses - it makes tracking everything SO much easier. And start keeping a simple spreadsheet or use an app to track every business expense from day one. Even small things like office supplies, software subscriptions, and mileage add up quickly. One thing I wish someone had told me: if you're making $38-50K in freelance income, you're definitely going to owe self-employment tax (15.3%) on top of regular income tax. Make sure whatever method you choose accounts for both!

I went through something very similar with a class action settlement from a defective smartphone case that damaged my phone back in 2022. Got $1,200 in late 2024 as reimbursement for the repair costs I paid out of pocket. The confusion around tax implications is totally understandable! In my case, I did receive a 1099-MISC in late January showing the full settlement amount. Following the advice of my tax preparer, I reported it on Schedule 1 as "Other Income" but then subtracted the same amount as a negative adjustment with the description "Class action settlement - recovery of repair costs." The key thing that helped me was keeping meticulous records of my original repair receipts and the settlement agreement language that specifically stated it was reimbursement for damages. Even though the 1099 made it look like taxable income, the documentation clearly showed it was just recovering money I had already spent. Don't stress too much about the W9 - like others mentioned, they collect everyone's info but the form itself doesn't determine taxability. The nature of what the settlement represents (reimbursement vs. punitive damages) is what matters for tax purposes. Since yours is clearly covering repair expenses you already paid, you should be in good shape!

I've been following this thread as someone who recently received a class action settlement as well, and wanted to add a few practical tips based on my experience with a medical device settlement last year. First, regarding the W9 timing - in my case, there was about a 6-week gap between submitting the W9 and receiving the 1099-MISC. The settlement administrator told me they batch process these forms, so don't worry if it seems like a long wait after submitting your paperwork. Second, when you do receive a 1099 (if you get one), take a photo or make a copy immediately. I learned this the hard way when my original got damaged and I had to request a duplicate, which delayed my tax filing by several weeks. Finally, for anyone using tax software to file, I found that TurboTax and H&R Block both have specific sections for handling settlement income that isn't actually taxable. Look for "Other Income" sections where you can add explanations - they've gotten better at guiding users through these situations since class action settlements have become more common. The consensus in this thread about keeping detailed records and not panicking about the 1099 is spot on. The settlement reimbursement itself isn't the issue - it's just making sure you report it correctly if you get the tax form!

Has anybody used TurboTax Self-Employed for Uber Eats? I heard it imports all ur earnings automatically but costs like $140. Is it worth it or should I just use FreeTaxUSA?

One thing that really helped me when I started with Uber Eats was setting up a separate savings account just for taxes. I automatically transfer 25-30% of each deposit into that account so I'm not scrambling come tax time. Also, don't forget about other deductible expenses beyond just mileage! Things like car washes (to keep your delivery car clean), phone chargers, hand sanitizer, masks, and even tolls can add up. I keep all my receipts in a shoebox and it's saved me hundreds. The key is to start tracking everything NOW - don't wait until tax season. Your future self will thank you! And seriously, those quarterly payments are crucial if you're making decent money. I learned that the hard way my first year.

Has anyone tried "Income Tax Planning" by Langdon, Albrecht, and Coyle? My friend recommended it but it's expensive and I want to make sure it's worth it before buying.

For a solid foundation without getting too overwhelmed, I'd suggest starting with "Taxes Made Simple" by Mike Piper. It's specifically designed for people who want to understand the fundamentals without needing an accounting degree. The author does a great job explaining concepts like marginal tax rates, deductions vs. credits, and different types of income in really plain language. Another excellent choice is "The Tax and Legal Playbook" by Mark Kohler - it covers both personal and business taxes with lots of real-world examples. What I like about it is that it explains not just how to follow the rules, but why certain tax strategies exist in the first place. If you end up doing any freelance work or side business, definitely pick up a copy of "Tax Savvy for Small Business" by Frederick Daily. It's become my go-to reference for understanding business deductions and self-employment tax calculations. The key is starting with one book that gives you the big picture, then diving deeper into specific areas as needed. Don't try to learn everything at once - taxes are complex enough that even professionals specialize in different areas!

Slightly different perspective - you could consider making an S-Corp election effective 1/1/24 even though it's past the deadline. The IRS allows for late S-Corp elections if you have "reasonable cause." Given that you were already operating as if you were an S-Corp (paying yourself W-2 wages), you might have a case for relief under Revenue Procedure 2013-30.

I went through almost the exact same situation last year! My SMLLC had been paying me W-2 wages for three years without S-Corp election. After panicking for weeks, I ended up working with a tax attorney who helped me file for late S-Corp election under Revenue Procedure 2013-30. The key was demonstrating that I had "reasonable cause" - specifically that I was operating in good faith as if I were an S-Corp (regular payroll, proper withholdings, etc.) but simply missed the technical filing requirement. We submitted Form 2553 with a detailed explanation letter showing my payroll records and explaining the misunderstanding. The IRS approved the retroactive election back to my original intended date, which meant I didn't have to amend any returns or deal with the Schedule C conversion. The whole process took about 6 months, but it was way less painful than I expected. Definitely worth exploring before you commit to amending multiple years of returns!