That's smart! Do you just use a regular spreadsheet or is there a template somewhere? Also, how do you handle documents that have multiple numbers on them like investment statements?

I just use a regular Excel or Google Sheets spreadsheet that I created myself. Nothing fancy, just those columns I mentioned. For complex documents like investment statements, I expand my tracking approach. I create sub-rows under the main document listing key figures (dividends, capital gains distributions, etc.) and note the specific form boxes where those numbers should go. Sometimes I even take screenshots of the tax software entry screens and note which box on my document goes to which field in the software. It's a bit more work upfront, but it saves me tons of confusion, especially for documents that have dozens of figures on them.

I used IRS Free File last year with W-2, some freelance income, and a small amount of stocks. It worked fine for me! Just make sure you go through the IRS website (irs.gov/freefile) rather than going directly to the tax company sites. If you go direct, they sometimes don't show the free options.

Thank you for this suggestion! I didn't even think about exemptions. Do I need to apply for these or are they automatic? Our county website is pretty awful and hard to navigate.

You almost always need to apply for exemptions - they're rarely automatic. Most homestead exemptions require an application within the first year or two of occupancy. Your county's tax assessor's office should have the forms, even if their website is terrible. It's worth calling them directly or visiting in person since these exemptions can save you significant money every year. Some counties also have partial exemptions for energy-efficient new construction, so ask about that too if your home has any green features. Don't wait on this - many exemptions have filing deadlines that, if missed, mean you'll have to wait until next tax year.

This is such an important point! I'm in Illinois and our property taxes are always paid in arrears. Made for a very confusing first year in our new build because the tax bills didn't match what we expected.

Omg you're right - we definitely go over 40 hours some weeks when there are more houses or deep cleans scheduled. I didn't even think about the overtime angle! How did you go about filing with the Department of Labor? Was it complicated?

Filing with the Department of Labor was surprisingly simple. I went to the DOL website and filed a wage complaint through their online system. You just need to provide details about your employer, your work hours, and how you were paid. After I submitted the complaint, a DOL investigator contacted me within a couple weeks. I shared my time records (I had kept my own log of hours worked in a notebook), and copies of payment records. They handled the entire investigation and calculated what I was owed. The whole process took about 3 months, but they recovered all my unpaid overtime plus damages.

While some workers might prefer contractor status for the deductions, that's not how tax law works. The IRS has specific criteria for worker classification regardless of what either party "prefers." If a worker meets the employee criteria (like OP clearly does), classifying them as a contractor is illegal tax evasion. Also, in this case, the workers can't even claim mileage deductions since the company provides the vehicles and pays for gas! They're getting all the downsides of contractor status (higher self-employment taxes, no benefits, no protections) with none of the advantages.

That's really helpful! So technically even if my divorce wasn't finalized until July, if we were living separately since 2022 and I meet those other criteria, I could potentially file as Head of Household? How would I document this if I get audited?

Yes, exactly! If you were living separately since 2022, and you meet all the other criteria I listed, you could potentially qualify as Head of Household even before the divorce was finalized. For documentation, keep records showing separate residences (lease/mortgage documents, utility bills), proof you paid more than half of household expenses (receipts, bank statements), and documentation showing your children lived with you for more than half the year (school records, medical records, childcare receipts). Also maintain any legal separation paperwork or documentation showing when your spouse moved out.

This is a really good point. I live in Missouri and they required me to use the same filing status for state and federal after my divorce, but I have a friend in Kansas who was able to file differently. Definitely check your specific state rules.

Thanks for confirming this happens in other states too! It's so confusing because tax software doesn't always warn you about this state-specific stuff. I spent hours redoing my returns last year because of this exact issue.

Is there anyway to estimate mileage after the fact if you didn't track it? I did some driving for Uber Eats but totally forgot to log miles.

Yes, you can estimate your mileage after the fact, but you need to be reasonable and have some basis for your estimate. If you have delivery history in your app, you can use that to reconstruct your mileage. Most delivery apps keep a record of your deliveries, so go through your history and map out the routes you took. Remember that you can count all business miles - driving to pickup locations, to customers, and returning to busy areas after deliveries. Just be careful not to include personal miles. If you're audited, the IRS will want to see some documentation, so create a log now with your best estimates and note that it's reconstructed. It's not ideal, but it's better than not claiming the deduction at all.

Keep ALL tax documents for at least 3 years after filing! That's the standard period the IRS can audit you. Some people recommend 7 years to be extra safe. Your tax person is right - don't throw them away!