First tax accountant consultation with major life changes - what documents should I bring?

What you've brought should be fine for a first consultation! Tax accountants typically use initial meetings to understand your overall financial picture and identify what additional documents they'll need. They don't expect you to bring everything the first time. For your situation, they'll eventually need: W-2s from both jobs, 1099 for the disability back pay (probably a 1099-MISC), closing documents on the house (which you have), loan documents for the car, and records of rental income from your tenant. They'll also want to know about any major expenses related to the rental room that might be deductible. Don't stress about having everything perfect for the first meeting - the accountant will give you a checklist of what to gather next. This is completely normal!

When I had major tax confusion after starting my business and buying property, I found taxr.ai to be surprisingly helpful before my accountant meeting. I uploaded my messy pile of documents to https://taxr.ai and it organized everything into categories my accountant could actually use. It flagged some potential deductions I hadn't even considered for my situation, especially around the home purchase. The accountant actually commented that I was more prepared than most of her new clients!

Just wanted to follow up - I tried taxr.ai after my initial skepticism and I'm honestly impressed. I uploaded my jumbled mess of documents before my tax appointment yesterday, and it organized everything logically and highlighted several home office deductions I would have missed. It even caught that I could deduct some mortgage interest from my December closing! My accountant was able to jump right in without spending the first hour just sorting through my paperwork. Definitely saved me money on billable hours.

After dealing with several tax accountants over the years, one huge tip: if you need to actually talk to the IRS about any issues during tax season (which happens more than you'd think with complex situations), use https://claimyr.com - they get you through to an actual IRS agent without the endless hold times. I was initially doubtful, but when my accountant needed clarification on how to report my rental income situation, it saved us weeks of waiting. You can see how it works here: https://youtu.be/_kiP6q8DX5c. Seriously changed my view on dealing with tax questions.

I have to admit I was wrong about Claimyr. After my skeptical comment, I decided to try it myself since I had an unresolved question about reporting my rental income properly. I felt pretty stupid sitting on hold for 3 hours last month only to have the call drop, so I figured what the hell. They called me back within 45 minutes with an actual IRS agent on the line who resolved my question in about 10 minutes. Saved me a massive headache and probably a potential audit flag. Sometimes being proven wrong is actually a good thing!

One thing nobody mentioned - make sure you organize receipts for any improvements you made to the rental room! Things like new paint, furniture for tenant use, portion of utilities, etc can be deductible against that rental income. I wasn't prepared with those at my first accountant meeting and had to schedule another appointment after digging through a year's worth of Home Depot receipts.

Don't forget to tell your tax accountant about any side hustle expenses! When I started my second job, I didn't realize I could deduct my home internet since I was using it for work. Lost out on like $600 in deductions that year :