I didn't use a payroll service last year, which is probably why I'm in this mess now! Do you know if these services can help with fixing past mistakes if I wasn't using them before? Or is it too late?

They can definitely help with past mistakes even if you weren't using them before! Both Homepay and SurePayroll offer "catch up" services where they'll help you file the missing forms from previous years. You'll need to provide them with the payment information for your household employee from 2023, and they can generate the proper W2 and W3 forms. They usually charge a one-time fee for this service rather than making you sign up for ongoing payroll. It's totally worth considering if you want to make sure everything gets done correctly without having to learn all the details yourself.

This is really important advice. I accidentally used the wrong year form once and it was a nightmare to fix. Another tip - keep copies of EVERYTHING you send to the SSA. I had to reference my copies when there was a mix-up with my household employee's Social Security earnings.

Do you have to create an account with the IRS to use their free fillable forms for the extension? And is it actually free or do they try to upsell you?

You do need to create an account on the Free File Fillable Forms site, but it's pretty straightforward. It's completely free with no upsells - it's the official IRS program. It's basically just the raw forms without any guidance, so the extension form (4868) is simple enough, but some people find the complete tax forms overwhelming without software guidance. For just the extension though, it's a great free option.

Yeah, filing an extension will definitely delay your refund since the IRS won't process your actual return until you submit it. The extension just gives you more time to file the paperwork, but your refund won't be processed until after you submit your complete return.

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.

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.

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.