That's really good to know about the account freezes! Do you know if other payment platforms like Venmo or Cash App have similar issues? Or would you recommend something completely different?

Venmo is actually owned by PayPal so they have similar policies. Cash App can be more flexible but still has its limitations. Many content creators use platforms specifically designed for their industry that have built-in payment processing - these tend to be much more stable since they're designed for that purpose. Some also use multiple payment methods to diversify risk. Another option is to set up a proper business entity (like an LLC) and get a business bank account. This provides an additional layer of separation between your personal finances and business activities, and gives you more professional payment options. It costs a bit to set up but provides much better protection and legitimacy.

Is there a minimum amount you need to earn before worrying about quarterly payments? I do some freelance work but it's pretty irregular and not a ton of money.

We actually do have some student loan interest from my wife going back to school part-time! I completely forgot about that. And I think we might qualify for the child care credit since we pay for after-school programs. Do you know if TurboTax automatically checks for these or do we need to specifically enter them somewhere?

TurboTax should ask about these items during the interview process, but sometimes it's easy to miss them if you're rushing through. Look specifically for the "Deductions & Credits" section in TurboTax and make sure you go through every category. For student loan interest, you should have received a Form 1098-E from the loan servicer showing how much interest was paid last year. For child care expenses, you'll definitely need to enter those manually. Look for the Child and Dependent Care Credit section. You'll need the provider's tax ID number and the total you paid for each child. This credit can be worth up to $1,200 per child depending on your income, so it could significantly reduce what you owe!

This is really helpful! Does filing Form 2210 complicate your return though? I've always been nervous about filing anything that might increase audit risk.

Does the free version still try to upsell you every five minutes like TurboTax does? I started using their "free" version last year and ended up paying $89 because of some "required upgrade" halfway through.

The IRS Free File options are genuinely free if you meet the income requirements. They're different from going directly to TurboTax or H&R Block's websites, where they often use the word "free" but then upsell you. You need to start through the IRS Free File portal (search "IRS Free File") rather than going directly to the tax software sites. This ensures you get the truly free version that's part of their agreement with the IRS. I've completed my 1040 filing three years in a row without paying a penny using this method.

The EITC income limit for single filers with no qualifying children is way lower than $32k though - I think it's around $17k. So they probably wouldn't qualify unless they have kids?

Is that really still a concern? I thought the IRS has basically accepted the backdoor Roth as legitimate at this point. I've been doing immediate conversions (like within a day or two) for years and never had any issues. Do you have any actual examples of the IRS challenging someone on this?

While the IRS hasn't been actively enforcing the step transaction doctrine against backdoor Roth conversions, it remains a theoretical risk because they've never explicitly blessed the strategy in official guidance. You're right that many people do immediate conversions without issues - the risk is very low. However, for someone who wants to be absolutely cautious, waiting a statement cycle is a reasonable precaution. The Tax Cuts and Jobs Act congressional commentary actually acknowledged the backdoor Roth strategy, which many tax professionals view as implicit approval, but it's not the same as explicit IRS guidance. What I tell clients is to make their own risk assessment - if you're comfortable with the small risk, immediate conversion is fine.

For 2025, if you're covered by a retirement plan at work, the deduction phase-out range for Traditional IRA contributions is $77,000-$87,000 for single filers and $123,000-$143,000 for married filing jointly. At $120k single, you'd be completely phased out, but if you're married, you might be able to take a partial deduction. If you're not covered by a workplace retirement plan, different limits apply. Either way, if you can't deduct it, backdoor Roth makes sense since you'd be making non-deductible contributions anyway.

Thanks for sharing your experience! Did FreeTaxUSA make it easy to figure out how to divide the income between states? I'm worried I'll mess that up since some of my unemployment was while I was preparing to move but technically still in Michigan.

It really does make it pretty straightforward! When you enter your W-2 information, it asks which state the income was earned in, and when you enter your 1099-G for unemployment, it asks similar questions. For the unemployment specifically, you'll need to allocate it based on where you were living when you received it. So if you received unemployment payments while still physically living in Michigan (even if you were planning to move), those payments would be considered Michigan income. FreeTaxUSA asks for your residency dates for each state and then guides you through allocating everything correctly. Just make sure you know which unemployment payments came when, so you can properly assign them to the right state.

I disagree - paying for a CPA seems excessive for this situation. I had a similar multi-state situation and FreeTaxUSA worked fine. Just take your time and read each question carefully. Maybe have a friend who's good with taxes review it before submitting if you're worried.