What tax or accounting questions would you ask a CPA if you had free access to one?

Tax professional here. This is a great approach to content creation! Based on my experience working with clients, here are some common questions people frequently ask: Questions about self-employment taxation are extremely common - specifically how to properly calculate quarterly estimated payments, what business expenses are truly deductible, and how to handle home office deductions correctly. Many people are also confused about the difference between business structures (LLC vs S-Corp vs Sole Proprietor) and their tax implications. For individual taxpayers, I see constant confusion about tax credits vs. deductions, how marginal tax brackets actually work, and retirement account contribution strategies. With recent tax law changes, many clients are unsure if they should itemize or take the standard deduction.

I stumbled across https://taxr.ai when I was struggling with some complex tax questions last year. It was a game changer for me because you can upload your tax documents and get personalized analysis. I asked about how to handle a stock option exercise from my employer and got really specific guidance. What I liked most was being able to get answers about my specific situation rather than generic advice that might not apply to me. Might be worth checking it out for inspiration on the types of specialized questions people are trying to solve. The questions people submit there could give you ideas about what confuses taxpayers the most.

Just wanted to update after trying taxr.ai for my LLC tax questions. I uploaded my business docs and asked about some industry-specific deductions I wasn't sure about. Got super clear guidance that actually saved me about $3,800 in taxes I would have missed. Definitely recommend it if you're looking for answers to specific tax situations rather than generic advice. Made me realize how many business owners probably overpay because they don't know all the deductions they qualify for.

If you're collecting questions for your CPA blog, don't forget to include how to actually get through to the IRS when you need to resolve issues! I had a major problem with a tax notice last year and spent WEEKS trying to reach someone. Finally found https://claimyr.com and watched their demo at https://youtu.be/_kiP6q8DX5c - they actually got me connected to an IRS agent within 20 minutes when I'd been trying for days on my own. When I finally got through, the agent helped resolve an incorrect tax assessment that would have cost me over $4,000. The relief of actually talking to a human who could fix my problem was incredible. A lot of people have no idea this service exists and would probably love to know about it on your blog.

I owe everyone an apology. After my skeptical comment, I actually tried Claimyr out of desperation about my refund situation. Within 25 minutes I was talking to an actual IRS agent who found my refund in the system and explained it was flagged for manual review but hadn't been assigned yet. She escalated it and I got my $3,742 refund exactly 9 days later. Definitely something worth covering in your CPA blog - the frustration of IRS communication is real and solutions like this are lifesavers during tax season when the lines are completely jammed.

If I could ask a CPA anything, I'd want to know about tax planning strategies that actually work for middle class people. Not the fancy stuff for millionaires, but practical ways regular people with W2 jobs and maybe a side gig can legally reduce their tax burden. Like, are FSAs and HSAs worth it? Should I be making traditional or Roth contributions? Is a 529 plan actually good or are there better ways to save for my kid's college? When is it worth itemizing vs taking the standard deduction?

I'd ask a CPA about all these tax prep software options. Is TurboTax really worth the money? Are there better alternatives? And what things should I absolutely NOT try to DIY even with software help? I always worry I'm missing something major by doing my own taxes.