Anyone know if a $0 conversion affects the 5-year rule for Roth IRA withdrawals? Like if I convert my empty Traditional IRA to Roth now, then make actual contributions in a few months, does the 5-year clock start now or when I make my first contribution?

Just to add another perspective here - I went through this exact situation last year and wanted to share what I learned. Even though you're converting $0, make sure to keep really good records of the conversion date and any paperwork from your custodian. The IRS likes to see a clear paper trail, especially for retirement account transactions. I'd recommend taking screenshots of your account before and after the conversion showing the $0 balance, and saving any confirmation emails or letters from your bank/brokerage. This documentation becomes super helpful if you ever need to prove the conversion happened and when it occurred. Also, double-check with your custodian about any fees for the conversion process itself. Some institutions charge administrative fees even for $0 balance conversions, which could actually result in a negative balance that you'd need to cover. Better to know upfront than get surprised later!

Just to add another perspective - I've been doing multiple side hustles for about 3 years now and learned this the hard way my first year. You absolutely need to report ALL income, even if it's just $20 from a random odd job. The $600 thing that confuses everyone is just about when companies are required to send you tax forms, not when you're required to report. What really helped me was setting up a simple spreadsheet at the beginning of each year with columns for date, source, amount, and any expenses. I update it weekly so I don't forget anything. Even for cash jobs where there's no paper trail, I still log it. The IRS expects you to track and report everything, and honestly it's not worth the risk of an audit over unreported income. For your eBay sales of personal items, as long as you're selling them for less than you paid originally, that's not taxable income since there's no profit. But your delivery driving, streaming tips, and creator earnings all need to be reported regardless of the amounts.

This is exactly the kind of confusion that trips up so many gig workers! I went through the same thing when I started doing multiple side hustles. The key thing to remember is that the $600 threshold is NOT about when YOU need to report income - it's about when companies are required to send YOU tax forms. You need to report ALL income from every source, no matter how small. So yes, your delivery driving, streaming tips, and content creator earnings all need to be reported, even if some are under $600 individually. For your eBay/Marketplace sales, if you're just selling personal items for less than you originally paid for them, those aren't taxable since there's no profit involved. But if you're flipping items or made any profit, then those sales count as income too. My advice: start keeping a simple log of all your income sources now. Even a basic spreadsheet with date, source, and amount will save you so much headache come tax time. And don't forget you can deduct legitimate business expenses like mileage for delivery driving, equipment for content creation, etc. Good luck!

Thanks everyone for all the detailed responses! This has been incredibly helpful. Based on what I'm reading, it sounds like my original idea of buying $25K worth of stamps was way too aggressive and would likely raise red flags with the IRS. I think I'll stick closer to what Miguel and Zainab suggested - maybe buy 6-12 months worth at a time based on my actual usage patterns. Last year I spent about $10K on postage, so maybe I'll do a $5K bulk purchase of Forever stamps at the end of this year and track usage carefully. The storage concerns Miguel raised are definitely something I hadn't considered either. I live in Florida so humidity is always an issue - definitely don't want thousands of dollars worth of stamps getting ruined! Has anyone used a specific system or app to track stamp usage over time? I want to make sure I have good documentation in case of an audit.

Hey Isabella! For tracking stamp usage, I've found that keeping a simple log works best for audit purposes. I use a basic spreadsheet with columns for: Date Purchased, Quantity, Cost, Date Used, Order/Customer ID (if applicable), and Running Balance. The key thing the IRS wants to see is that you're using the stamps for legitimate business purposes, so I also note what type of shipment each stamp was used for (customer order, business correspondence, etc.). One tip from my accountant - take a photo of your stamp storage setup and keep it with your records. This shows you're properly maintaining the inventory and treating it as a business asset rather than just hoarding stamps as an investment. Since you're in Florida with the humidity concerns, definitely invest in some airtight containers with desiccant packets. I learned this the hard way when some of my stamps got sticky and unusable - had to write off about $200 worth as a loss, which was a pain to document properly for taxes! Your $5K purchase plan sounds much more reasonable than the original $25K idea. That should give you plenty of inventory without raising any red flags with the IRS.

Has anyone actually tried getting their transcripts directly from the IRS website recently? I keep reading horror stories about identity verification problems.

I went through this exact same situation about 6 months ago when I was refinancing my home! Here's what worked for me: First, definitely try logging into your TurboTax account - they keep copies of your returns for several years and you can download them immediately as PDFs. Since you used them for the last 3 years, this should cover your 2022 and 2023 returns that your lender specifically requested. For the older H&R Block returns, if you filed at a physical location, definitely call them first before going the IRS route. When I called my local H&R Block office, they were able to email me copies of my 2019 and 2020 returns the same day for $25 each. If those options don't work out, the IRS transcript route that others mentioned is solid. I had to do this for one year where my tax preparer had gone out of business. The online system worked fine for me, but if you run into ID verification issues, you can always request by mail using Form 4506-T - it's free and took about 2 weeks when I did it. Pro tip: Call your mortgage lender and explain the situation. Many will accept tax transcripts instead of full returns, and some will even give you a short extension on document deadlines if you can show you've already requested the transcripts. Good luck with your closing!

One thing nobody mentioned yet - make sure you're paying quarterly estimated taxes on your tutoring income! I got hit with an underpayment penalty my first year as a contractor because I didn't realize I needed to make payments throughout the year.

As someone who's been doing freelance consulting work for a few years, I can confirm that the QBI deduction is a real game-changer for independent contractors like yourself! Your tutoring income absolutely qualifies. One thing I'd add to the excellent advice already given - since you're working 30 hours a week, this is clearly a substantial business activity, not just a hobby. That strengthens your position for claiming business deductions. Also, don't stress too much about the complexity. The IRS has Publication 535 (Business Expenses) and Publication 587 (Business Use of Your Home) that explain everything in detail, but honestly, most tax software will walk you through the QBI calculation once you enter your Schedule C information. The key point everyone's made is correct - at your income levels, you should get the full 20% QBI deduction, which on $23,500 would be up to $4,700 in additional deduction. That's significant money! Since your deadline is approaching, focus on getting your Schedule C completed first (your tutoring income and any business expenses), then the QBI deduction will flow from there. You've got this!