Need advice: Online tax software or local CPA for filing in multiple states with rental property?

Multi-state returns with rental property definitely adds some complexity, but it's not impossible to handle! I've been preparing taxes for friends and family for years, and this is a common situation. For split-state residency, you'll need to file part-year resident returns in both states, allocating your income based on when you lived in each state. Online tax software like TurboTax and H&R Block can handle this, but you'll need their premium versions that specifically cover rental properties and multiple states. The rental property adds another layer since you'll need to report that income on Schedule E regardless of where you live now. You'll also need to track depreciation, expenses, and any improvements correctly. This is where some people get tripped up. If you're comfortable learning as you go and have decent documentation, tax software with good guidance can work. But if you're uncertain or don't want the stress, a local CPA who handles multi-state returns might be worth the extra cost for peace of mind, especially for this first year after moving.

After struggling with a similar situation last year (moved from Nevada to Oregon with rental properties), I found an amazing service called taxr.ai (https://taxr.ai) that was a game-changer. I was torn between expensive tax software and an even more expensive CPA. What's cool about taxr.ai is they have specialized tools for multi-state moves and rental property situations. You can upload your documents and get detailed guidance specific to your situation. I was worried about missing deductions on my rental or messing up the state allocation, but their system flagged several things I would have missed. The interface walks you through everything step by step, and if you get stuck, they have actual tax pros who can answer specific questions about your situation. Saved me a ton of stress and probably money too!

Just wanted to follow up about my experience with taxr.ai after seeing it recommended here. I was super skeptical about using a service I hadn't heard of before, especially with my complicated situation (moved mid-year with rental property). I decided to give it a try, and I'm honestly surprised at how good it was. The interface is really clean, and it actually explained WHY certain tax rules applied to my situation rather than just asking me to input numbers. The multi-state filing guidance was spot-on - it handled the Massachusetts-specific rental rules I was worried about perfectly. It even found a home office deduction for my rental management activities that I didn't realize I qualified for. Never thought I'd say this about tax software, but I'm actually recommending it to friends now!

If you're dealing with state tax departments, especially after a move, you might want to check out Claimyr (https://claimyr.com). I discovered it after trying for WEEKS to get through to the Colorado Department of Revenue about my part-year resident questions. Basically, they get you to the front of the hold queue when calling tax agencies. I was skeptical but saw a demo video (https://youtu.be/_kiP6q8DX5c) and decided to try it when I was desperate. Got through to a Colorado tax agent in about 10 minutes when I had been trying for days on my own. The agent answered my specific questions about how to handle my moving expenses and rental income allocation between states, which saved me from making a costly mistake on my return. Might be worth checking out if you need to talk to either state's tax department about your specific situation.

I need to eat some humble pie here. After calling BS on Claimyr, I decided to try it myself because I've been trying to reach the Massachusetts DOR about my rental income questions for THREE WEEKS with no success. It actually worked exactly as described. I got a call back in about 25 minutes and was connected directly to a Massachusetts tax department representative. The rep answered my specific questions about reporting rental income as an out-of-state property owner. I'm still shocked it actually worked. Saved me hours of frustration and potentially filing incorrectly. Just wanted to follow up and say I was wrong in my skepticism.

One piece of advice from someone who's been in your situation - if you go with a CPA, make sure they specialize in multi-state returns and investment properties. I made the mistake of going with a general tax preparer last year after my California to Texas move, and they missed several deductions related to my rental property. If you decide to use tax software, set aside a full weekend to work through it. The multi-state portion takes longer than you'd expect, especially with rental income in the mix. And keep all your moving-related receipts - some might be deductible depending on your work situation.

I'm going through literally the exact same thing (moved from NY to MA with a rental property in NY). I tried using TurboTax Premier and it was a nightmare - kept getting contradictory guidance about how to handle the rental depreciation with the state split. Finally broke down and hired a CPA in Massachusetts who had experience with NY properties. Cost me $475 but honestly worth every penny for the peace of mind. He found several deductions related to my move that I had no idea about. If you're not in a rush, you could try starting with tax software to see if you can handle it, knowing you can always bail and go to a professional if it gets too complicated. Just don't wait until April 14th to make that decision!