What about if I'm using my maiden name for business but my married name is on my social security card? Will that cause problems?

That's exactly the kind of situation that causes tax matching problems. You should use your legal name (the one on your Social Security card) on the first line of the W-9 form. If you're using your maiden name as a business name, you would put that on the second line "Business name/disregarded entity name." Ideally, you should consider filing for a proper DBA ("doing business as") with your local government if you're consistently using your maiden name for business purposes. This creates a clear paper trail between your legal name and business name.

You typically only need to provide a W-9 once unless your information changes (like a new address, name change, or tax ID change). Some companies have policies requiring annual updates just to ensure they have current information, but it's not an IRS requirement. It's not unusual for a client to request an updated form each year - they're just being thorough with their record-keeping. If nothing has changed in your information, you can just complete a new form with the same details.

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 this something you have to specifically request? I paid a similar notice last year and no one mentioned anything about penalty abatement to me. I had a perfect tax record before that too.

Yes, you absolutely have to specifically request penalty abatement - the IRS will almost never offer it voluntarily! It's not widely advertised, but it's an official IRS administrative waiver. Many people qualify but never know to ask for it. If you paid penalties within the last 2-3 years and had a clean record before that, you might be able to request a retroactive abatement and get those penalties refunded. You'd need to call the IRS and specifically request "First Time Penalty Abatement" for the tax year in question, explaining that you had a good compliance history before that. It's definitely worth trying!

This is solid advice. I work in a tax office and we see this all the time. People bring in final collection notices for issues that could have been easily resolved months earlier. By that point, options are much more limited and the amounts owed have usually increased significantly.

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!

TurboTax does have a rental property section where you can add depreciable assets, but it's pretty basic. It doesn't handle tracking the disposal of individual furniture items well over multiple years. I switched to TaxAct which has slightly better rental property features, but still had to maintain a separate spreadsheet for tracking my furniture items.

Thanks for that info! Sounds like I might need to keep a separate tracking system regardless of which tax software I use. I'm guessing none of the consumer tax programs really handle the complexity of multiple furniture items with different depreciation schedules and disposal dates.