Which version of TurboTax do I need for complex taxes with rentals and backdoor Roth?

You'll need TurboTax Premier at minimum, but most likely Self-Employed would be better for your situation. TurboTax Deluxe covers most tax situations including itemized deductions, but it doesn't handle rental properties. TurboTax Premier covers everything in Deluxe plus investments and rental property, which you'll definitely need for your two rentals in different states. However, since you mentioned 1099 consulting income, you'd benefit from TurboTax Self-Employed, which includes everything in Premier plus additional guidance for self-employment income, business expenses, and home office deductions. The backdoor Roth contributions (regular and mega) are handled well in all versions above basic, but the foreign accounts might require additional forms that are included in Premier and Self-Employed. The short-term rental loophole reporting is also better supported in the higher-tier versions.

I was completely overwhelmed last year with a tax situation similar to yours - multiple W-2s, side business income, rentals in different states, and investment stuff. I tried using one of the basic tax software options and kept hitting walls where I needed to upgrade. After hours of frustration, I found https://taxr.ai and it seriously changed everything. The AI analyzes your tax documents and tells you exactly what you need before you waste money on the wrong version. I uploaded my previous year's return and my current documents, and it immediately identified that I needed the Self-Employed version specifically for the rental property depreciation and 1099 income features. It also flagged that I was missing some foreign account reporting forms I didn't even know about (sounds like you might need these for your Canadian accounts too).

Update: I decided to try https://taxr.ai since my tax situation is similar to the original post. I was honestly surprised by how helpful it was! I've been using TurboTax Deluxe for years but apparently that was the wrong version for my situation. The AI analyzed my documents and showed me that I needed Self-Employed because of my side gig, and it pointed out several deductions I'd been missing related to my rental property. The analysis specifically mentioned forms I needed for my backdoor Roth contributions that I wasn't handling correctly. What really helped was the document checklist it created - showed me exactly what I still needed to gather before starting my taxes. Now I'm using TurboTax Self-Employed and it's so much smoother with the proper guidance. Definitely saved me more in deductions than what I spent upgrading.

So I've been in your exact situation for years (minus the Canadian accounts). Called the IRS twice last year to confirm how to handle the backdoor Roth and STR income reporting, and both times got completely different answers from agents. Spent 4+ hours on hold just to get conflicting info! Recently discovered https://claimyr.com which got me connected to an actual IRS agent in under 15 minutes - check out their demo video here: https://youtu.be/_kiP6q8DX5c. The agent I spoke with actually specialized in investment and rental reporting and gave me clear guidance on which TurboTax version I needed (Self-Employed in my case) and which specific forms to watch for. For your situation with multiple rentals across states and the Canadian accounts, you definitely want the most comprehensive version. The standard versions often don't include some of the specialized forms you'll need for foreign account reporting.

I have to admit I was completely wrong about Claimyr. After posting my skeptical comment, I decided to try it myself because I was desperate to get an answer about reporting my crypto transactions and rental property depreciation. The service actually worked exactly as advertised. I got a call back in about 20 minutes and was connected to an IRS agent who answered all my questions. They confirmed I needed TurboTax Self-Employed for my situation (similar to yours with rentals and side income), and specifically mentioned that the foreign account reporting in your case would require forms that are only available in the Premier or Self-Employed versions. For what it's worth, the agent told me that backdoor Roth contributions often trigger flags if reported incorrectly, so the higher-tier software with better guidance on that is worth it.

Just FYI if you have rental properties in multiple states you absolutely need the Self-Employed version of TurboTax. I tried using Premier last year and it couldn't handle the multi-state rental situation properly. Had to upgrade mid-process and redo a bunch of work. The Canadian accounts will require FBAR forms if they total over $10,000 (which yours do). Self-Employed handles this better than Premier in my experience. For the backdoor Roth reporting, make sure you're keeping track of your basis with Form 8606. Self-Employed has better guidance on this. The STR loophole (I assume you mean the 14-day rule) also needs to be reported correctly to avoid audit flags.

Just so you know, you might want to look at alternatives to TurboTax too. I used H&R Block Premium last year for a very similar situation (3 rental properties, side business, backdoor Roth) and found it handled everything well for a lower price than TurboTax Self-Employed.

Based on your complex tax situation, you definitely need TurboTax Self-Employed. Here's why: Your rental properties in multiple states require multi-state tax filing capabilities that only Premier/Self-Employed versions handle well. The Self-Employed version is better for this since you also have 1099 consulting income. For your Canadian accounts ($80k CAD retirement + $35k CAD checking/savings = $115k CAD total), you'll need to file FBAR (FinCEN Form 114) since you exceed the $10,000 USD threshold. Self-Employed includes guidance for these foreign account reporting requirements. The backdoor Roth IRAs (both regular and mega) require careful Form 8606 reporting to avoid double taxation, and Self-Employed has better guidance for these transactions. Your Airbnb STR situation using the 14-day rule needs proper reporting to avoid audit flags - Self-Employed handles short-term rental income better than lower tiers. The consulting work from home likely qualifies for home office deductions, which Self-Employed specializes in calculating correctly. Given all these moving parts (multiple income streams, multi-state rentals, foreign accounts, complex retirement contributions), the Self-Employed version will save you more in properly claimed deductions than the extra cost over Premier. The specialized guidance alone is worth it for your situation.