Thanks for this! Question - do you know if I need to keep all the receipts from the post office for shipping costs or can I just use the eBay records that show what I spent on shipping?

You can absolutely use the eBay records that show shipping costs! eBay keeps excellent records of all shipping labels purchased through their platform, and those records are sufficient documentation for the IRS. Just download your yearly selling record which includes all those shipping costs. For any shipping supplies or postage you purchased outside of eBay (like buying boxes or stamps separately), you should try to keep those receipts, but even a credit card statement showing purchases at office supply stores can serve as backup documentation.

I switched from TurboTax to FreeTaxUSA last year for my eBay business. TurboTax wanted to charge me $120+ for the self-employment version, while FreeTaxUSA was way cheaper and handled Schedule C just fine.

Where do you find this form? I looked on the healthcare.gov site and couldn't locate an EO-001 form.

I tried this route once and the insurance company told me they couldn't help with 1095-A forms since those come directly from the Marketplace. They only deal with 1095-B forms for non-Marketplace coverage they provide. They did suggest contacting my state's Department of Insurance consumer assistance program, which surprisingly was helpful in escalating my case with the Marketplace. Might be worth trying if you're hitting walls with the regular channels.

That's what I'm worried about. I really need this job and don't want to burn bridges, but I also don't want to pay extra taxes I shouldn't have to pay. Did you end up having to pay the full self-employment tax before the IRS determination came through?

I actually used Form 8919 when I filed my taxes, which allowed me to only pay the employee portion of the Social Security and Medicare taxes while my SS-8 determination was pending. That way I didn't have to pay the full self-employment tax. If the IRS had eventually determined I was actually a contractor (which they didn't), I would have had to pay the difference later. But it allowed me to file on time without overpaying. My tax preparer was familiar with the situation and helped me with the proper coding on the form.

I tried this approach with my employer last year and it worked! Sometimes people just don't know the rules. I printed out the relevant IRS publication and highlighted the parts about household employees. When I showed them, they were actually relieved to have clear guidance and issued me a correct W-2.

Do you know if homeowner's insurance premiums are ever tax deductible? I think I prepaid 14 months at closing and wondering if any of that is deductible anywhere.

Unfortunately, homeowner's insurance premiums aren't tax deductible for personal residences. They're considered a personal expense rather than a deductible housing expense. The only exception would be if you use part of your home for business - then you might be able to deduct the business portion of your insurance. However, if you paid for mortgage insurance premiums (different from homeowner's insurance), those might be deductible depending on your income level and when you got your mortgage. The rules change frequently on mortgage insurance deductibility, so that's worth looking into for your specific situation.

In my experience, most lenders only issue a 1098 if the total interest for the year exceeds $600. If you closed in late December, the few days of interest probably didn't hit that threshold, so they might have just included it in next year's form. You can still deduct it in the correct year though, even without a separate 1098.

Would you say the same applies for H&R Block? I've always used them in-person because I'm paranoid about making mistakes, but it costs me around $350 each year for what seems like a pretty simple return.

H&R Block's storefront preparers are generally not CPAs but trained tax preparers with varying experience levels. They're in a middle ground - more personalized than software but typically less knowledgeable than a dedicated CPA. For a straightforward return, you're probably overpaying at $350. Their software is on par with TurboTax but much cheaper, around $50-100 depending on the version. If you're comfortable trying software but want some backup, H&R Block does offer a hybrid option where you can start online but get help from a tax pro if needed. Bottom line: If your return is fairly simple, either tax software or the AI tool mentioned would likely be more cost-effective than continuing to pay $350 at H&R Block. But if that peace of mind is worth $250+ to you each year, there's value in that too!

This isn't entirely accurate. The $73k limit is for the IRS Free File program partners, but TurboTax actually left that program last year. They have their own "free" version but it's very limited in what forms it supports. With education expenses and retirement account transfers, OP would definitely get bumped to a paid tier.