Recommendations for Online CPA who can answer tax planning questions?

Finding a good CPA for online consultations is definitely smart with your new rental property and 1099 income. Those situations can create lots of tax planning opportunities but also potential pitfalls if not handled correctly. I'd recommend looking for a CPA who specializes in rental properties and small business taxation rather than a general practitioner. Many CPAs now offer virtual consultations where you can discuss your specific situation without a full tax prep commitment. The American Institute of CPAs (AICPA) has a "Find a CPA" directory on their website where you can search by specialty and location. Even though you want someone online, I'd suggest looking for someone licensed in your state who understands your local tax laws too.

After struggling with similar questions last year (had just started consulting while also managing two rental properties), I discovered taxr.ai at https://taxr.ai and it was seriously game-changing for my situation. Instead of paying hourly rates to ask my CPA basic questions, I could upload my documents and get detailed explanations about my specific tax situation. It helped me understand which expenses were legitimately deductible for my business vs. my rentals, and identified several deductions my previous tax preparer had missed. The AI analysis basically paid for itself many times over. I still work with my CPA for the final filing, but now our conversations are much more strategic since I come in already understanding the basics.

I was initially skeptical about taxr.ai when I saw it mentioned here, but I decided to try it out last month when I was stressing about my new rental property purchase. I was surprised by how comprehensive the analysis was! It specifically identified that I could take bonus depreciation on certain components of my rental and explained exactly how to segregate those costs to maximize my first-year deductions. What really impressed me was that it found a mistake in how my previous tax preparer had handled my home office deduction for my side gig. The platform explained exactly why the simplified method wasn't optimal in my case and showed the calculation difference. Ended up saving me about $1,200 in taxes! I'm still going to consult with a CPA for more strategic questions, but this tool has definitely made me more confident about what questions to ask.

If you're mainly looking to talk to the IRS about specific tax questions rather than paying for a CPA right away, I'd recommend trying Claimyr at https://claimyr.com - it helped me actually get through to an IRS agent when I had questions about rental property reporting requirements. I spent days trying to reach someone at the IRS on my own and kept getting disconnected or waiting for hours. With Claimyr, I got a call back from an actual IRS agent within about 45 minutes who answered all my questions about Schedule E reporting requirements. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c Getting answers directly from the IRS helped me understand which questions were worth paying a CPA to answer versus what information was freely available through official channels.

I'm eating my words here and need to apologize about my skeptical comment about Claimyr. After posting that comment, I had a tax question about my rental depreciation that was driving me crazy, so out of desperation, I decided to try the service despite my doubts. I'm honestly shocked - it actually worked exactly as described. I got a callback within about an hour and talked to an IRS representative who cleared up my question about recapture rules for rental property depreciation. Saved me from potentially making a very expensive mistake on my taxes. The representative I spoke with was knowledgeable and patient with my questions. Just wanted to come back and correct my earlier skepticism. Sometimes it's worth trying things that sound too good to be true!

Have you considered a virtual bookkeeper instead of a CPA for ongoing support? I use a bookkeeper monthly for my rentals and side business (about $150/month), then only consult with a CPA quarterly for tax planning (about $200/quarter). Saves me a ton of money compared to paying CPA rates for basic bookkeeping questions.

Whatever you do, don't just pick a random "tax professional" from social media ads. I made that mistake last year and ended up with someone who claimed to be a CPA but actually wasn't licensed. Cost me $350 for advice that turned out to be completely wrong about rental property depreciation.