This sounds like a great option! Do they have income limits for who qualifies? And do they help with state returns as well as federal?

They prioritize seniors but don't have strict income limits. Generally, they serve people with "low to moderate" income, which in practice can be up to $75,000 for individuals or $100,000 for families, but this varies by location based on the cost of living in your area. They absolutely help with state returns as well as federal. The service is completely free regardless of how complex your return is. Just be aware that during peak season (late March through April 15) the wait times can get long, so going earlier in the season is better if possible.

When I was searching for a reviewer, I asked specifically, "What's your process for reviewing a self-prepared return?" The good ones will explain a systematic approach and mention specific areas they focus on. Also ask, "How often do you find missed opportunities on DIY returns?" - the honest ones will have specific examples ready.

That's really helpful advice, thanks! I like the idea of asking about their process upfront - that would definitely help identify who's just going to skim it versus who takes the review seriously. I'll definitely try those questions if I decide to get a review again this year. I still feel a bit burned by the experience, but maybe I just chose the wrong professional. I've seen a few recommendations in this thread that seem promising too.

The key to avoiding the hobby loss rule is showing that you're running your D&D sessions as a business with the intent to make a profit. Keep good records, have separate business accounts, track all expenses properly, create a business plan, and be professional about how you operate. The IRS generally uses a "3 out of 5" guideline - if you show a profit in 3 out of 5 consecutive years, they typically consider it a legitimate business. Since OP mentioned they were "hit hard with taxes," it sounds like they're profitable, which helps their case significantly.

That makes sense, thanks! I've been profitable 2 of the last 3 years, so I think I'm on the right track. I do have separate tracking for all my game master income and expenses, but I should probably open a dedicated bank account to make it even clearer.

Thanks for the perspective! Did you find that you were able to itemize deductions right away in your first partial year of homeownership? Or did it take a full year of mortgage interest before it made sense?

In my first partial year, I wasn't able to itemize because I only had about 4 months of mortgage interest which wasn't enough to exceed the standard deduction. I just took the standard deduction that first year. It wasn't until my first full calendar year of homeownership that itemizing made sense. But it's still worth running the numbers both ways in TurboTax (itemized vs standard) to see which gives you the better outcome. The software makes this comparison pretty easy.

What states still have good homebuyer tax breaks? I'm in Pennsylvania and when I asked my lender they said there weren't any tax breaks, just loan programs for first-time buyers.

California still has some good ones! My friend just bought her first home and got a $10,000 credit through some state program. Definitely worth checking.

What exactly happens if you can't get someone to fill out a W-9? Like if they refuse or you just can't reach them anymore? Are you still supposed to issue the 1099 somehow?

If someone refuses to complete a W-9 or you can't reach them after payment, you're technically supposed to begin backup withholding at a rate of 24% on any future payments to that person. This means holding back that percentage and remitting it to the IRS. For the 1099-NEC, you should still issue it with whatever information you do have. If you're missing their tax ID number, the IRS may send you a B-notice requesting the missing information. The best protection is documenting your attempts to get their information (emails, certified letters, etc.). The IRS understands these situations happen, but they want to see you made a good faith effort to comply.

So what's the actual difference then? Like how much control can you have before they're considered an employee? I sometimes need people to be at certain places at certain times because, you know, that's when the client expects us.

Thanks for sharing your experience! When you say Schedule C might be better, does that mean you believe the education would qualify as a legitimate business expense under T Reg 1.162-5(a) for someone in this situation?

Yes, I believe it would qualify as a legitimate business expense in this specific case. The key is that T Reg 1.162-5(a) allows deductions for education that "maintains or improves skills required by the individual in his employment or other trade or business." If your client can document that they regularly perform accounting functions in their law practice (like tax planning, financial analysis for clients, etc.), then the CPA education enhances existing skills rather than qualifying them for a new profession. It's the actual tasks performed that matter, not the job title. I successfully took this position on my own return and have advised clients similarly without issues.

I don't think you can double-dip like that. IRS Publication 970 specifically says you can't claim an education credit and a business deduction for the same expense. You have to choose one or the other.