Is there a calculator or something that shows the break-even point between traditional vs Roth? I always hear conflicting advice and don't know how to figure out which is actually better for my situation.

There's no perfect calculator because it depends on assumptions about future tax rates that nobody can predict with certainty. However, a good rule of thumb is that if you expect your tax rate in retirement to be higher than it is now, go with Roth. If you expect it to be lower, go traditional. For young people early in their careers with relatively low incomes, Roth often makes more sense because they're likely in a lower tax bracket now than they will be in retirement. But everyone's situation is different - factors like pension income, Social Security, and other retirement income sources can affect your future tax situation.

This is exactly what I do too! It's called "tax diversification" and it means you'll have both tax-free and taxable income sources in retirement, which gives you flexibility for tax planning. Smart strategy.

This is super helpful, thank you! Do you know if I would need to file any US tax returns if I'm classified as a non-resident alien? And if I do submit a W-8BEN to PayPal, how long does it typically take for them to process it and stop the 30% withholding?

Yes, you would likely need to file Form 1040NR (U.S. Nonresident Alien Income Tax Return) if you have U.S. source income above certain thresholds, even as a non-resident alien. For income received through PayPal that's considered U.S. sourced, you'd generally need to report it. For the W-8BEN processing, PayPal usually takes about 1-2 weeks in my experience, though sometimes it can be faster. The tricky part is determining if your income through PayPal is actually U.S. sourced or not - it depends on where the services were performed or where the payer is located, not just where your PayPal account is based. If you're performing services while physically outside the U.S. for non-U.S. clients, that income might actually be foreign-sourced and not subject to U.S. taxation at all.

This is such a good point! I had a similar situation and ended up double paying taxes because I didn't understand the source rules. Does anyone know if there's a way to explain to PayPal that the income isn't US-sourced even though it's going into a US account?

Oh man, I hadn't even thought about the state implications. I'm in Illinois - do you know if they automatically recognize the federal S-corp election or do I need to file something separate with them too?

Illinois does generally conform to federal S-corp elections, but they still require their own notification. You need to file Form IL-1120-ST with the Illinois Department of Revenue, and they technically want you to submit this within 60 days of your federal election. Since your federal election is going to be retroactive, you should contact the Illinois Department of Revenue specifically about your situation. They may require you to file a separate late election acceptance for state purposes. Unlike some states that automatically accept the federal election, Illinois wants to be formally notified, even though they typically follow the federal tax treatment.

Any recommendations for finding a CPA who specializes in fixing these kinds of messes? I've been looking but everyone I talk to seems to have a different opinion on how to handle it.

Which app do you use for the receipts? I've tried a couple and they were garbage at organizing things properly.

I use Expensify for most things - it automatically extracts the vendor, date, and amount which saves tons of time. It also syncs with my accounting software. Before that I used QuickBooks' receipt capture feature, which was decent but not as good at recognizing text on receipts.

Amazon order history plus your credit card or bank statement showing the payment amount does work. I had an audit last year and this combo was accepted. Just make sure the amounts match and you can show the items were for business use. If it's a mixed order with personal items, highlight the business items specifically.

Thanks for the info! That's a huge relief since about half my office supplies are from Amazon and I've just been keeping the email receipts and order details page screenshots. Good to know that plus my credit card statements should cover me.

I actually double-checked this. The points were definitely on the original 1098 that I provided to my CPA. I found my copy and it clearly shows the points in Box 6. I think it was just an oversight on their part.

In that case, they definitely should fix this for free. Since you have proof the information was provided to them correctly on the original 1098, this is 100% their responsibility to correct without charging you. Make sure to emphasize that when you talk to them. If they give you any pushback, consider finding a new CPA next year. Mistakes happen, but how they handle fixing those mistakes tells you a lot about their professionalism.

That's only if the amendment changes your AGI significantly enough to affect your premium tax credit calculation. Adding mortgage points as a deduction would likely lower AGI, which could actually increase potential premium tax credits rather than reduce them.