Has anyone else noticed that TurboTax seems to handle the basis calculation differently than H&R Block software? When I had almost this exact same situation last year (contribution then loss before conversion), TurboTax carried forward the basis correctly, but when my brother used H&R Block, it seemed to miscalculate the basis after the loss. Just wondering if others have seen this?

I went through this exact same situation two years ago and it was so confusing at first! Your tax software is correct - that $200 on line 14 of Form 8606 represents your remaining basis in Traditional IRAs that carries forward to future years. Think of it this way: you put $7,000 of after-tax money into the Traditional IRA, but only converted $6,800 worth of value. The IRS recognizes that you still have $200 of "basis" (money you already paid taxes on) that wasn't converted yet. This $200 doesn't disappear - it's like a credit that reduces the taxable portion of any future Traditional IRA distributions or conversions. So if you do another backdoor Roth next year, that $200 will be added to your new contribution for basis calculation purposes. It's actually a small silver lining to the investment loss since it means less taxable income on future conversions. Just make sure to keep good records of your Form 8606 each year so you can track this basis properly!

Doesn't this also depend on whether the medical practice is an S-corp or sole proprietorship? I thought the rules were different.

Just want to add that timing matters a lot here too. Since your sister just purchased the building last year, she needs to be careful about how she handles the transition. If she's been using it for business since purchase, she should have been taking depreciation deductions on her Schedule C already. If she decides to go the separate entity route (like the LLC approach mentioned above), there could be tax implications for transferring the property from personal ownership to the LLC. This might trigger capital gains or other issues depending on how much the property has appreciated. Also, make sure she's aware of the passive activity loss rules if she goes with rental income - these can limit her ability to deduct losses from the rental property against her active medical practice income. The rules are pretty complex and depend on her level of participation in managing the property. Definitely worth getting professional advice before making any structural changes, especially since she's doing well financially. The wrong move could end up costing more than the potential tax savings.

Just wondering - does having a SSN from your internships change anything about how you fill out the W8-BEN? I got a social when I worked in the US last summer.

Just to add one more perspective here - don't stress too much about the W8-BEN form. It's actually pretty straightforward once you understand what it's for. The key thing to remember is that this form is specifically about the interest income your bank account generates, not your employment income. Since you're Canadian, you'll definitely benefit from the tax treaty. The US-Canada treaty eliminates withholding on bank interest entirely (0% instead of 30%), so filling out this form will actually save you money on any interest you earn. One thing I'd suggest is to keep a copy of your completed W8-BEN for your records. When you do eventually become a US tax resident (which sounds like it'll happen soon with your full-time move), you'll need to notify your bank and switch to providing them with a W-9 form instead. Having documentation of when you made that transition can be helpful for tax purposes. The form itself is valid for 3 years, but your circumstances are changing, so you'll likely need to update it sooner than that. Good luck with your move!

My situation was a little different but might be helpful. My 2017 divorce had both alimony and child support. In 2022, we modified BOTH the child support and alimony amounts because my income changed dramatically. My accountant warned me that because we modified the actual alimony amount after 2018, I lost the grandfather status and can no longer deduct it! So based on my experience, if your modification only touched child support and left alimony completely alone, you should be fine. But if you modified the alimony amount or terms at all, even in the same document as the child support changes, you might have lost the deduction.

This is exactly the kind of complex tax situation where the details really matter. Based on what you've described, since your 2023 modification was specifically for child support (due to your oldest graduating college and youngest changing schools) and your divorce was finalized in 2018, you should still be able to deduct your alimony payments. The key question is whether your modification document touched the alimony terms at all. If it only addressed the child support calculation and left the $2,250 monthly alimony amount and terms completely unchanged, then you maintain your grandfathered status under the pre-2019 rules. However, I'd strongly recommend getting a definitive answer before your quarterly payment deadline. You might want to review your modification paperwork carefully to see if it mentions alimony at all, or consider reaching out to the IRS directly for clarification on your specific situation. The peace of mind of knowing for certain is worth it when you're dealing with $27,000+ annually in deductions.

Call the IRS directly if ur unsure about anything. Better safe than sorry

Another telltale sign of this scam is the timing - legitimate EIP payments ended years ago, so any new messages claiming you're eligible for a $1,400 payment should be an immediate red flag. The IRS doesn't send out surprise payments via text, and they definitely don't ask you to "provide accurate personal information" through suspicious links. Always remember: if it sounds too good to be true and comes through an unexpected channel, it probably is a scam.