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.

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!

Any recommendations for good E&O insurance providers specifically for tax preparers? My quote from [insurance company] seemed crazy high.

Check out Insureon or NAEA's member insurance program if you're an Enrolled Agent. I've found the NAEA rates to be quite reasonable. Also look at Landy Insurance Group - they specialize in coverage for tax professionals and understand the specific risks. Make sure your policy covers representation during audits, not just errors. The difference in premiums isn't huge but the protection is significant. My premium is around $1,200/year for $1M in coverage, which is well worth the peace of mind.

That's a really good point about specializing. I've been wondering if the traditional tax office model will even exist in 10 years with all the AI stuff happening. Do you think it's still worth buying an existing practice with all these changes coming?

Thanks for sharing your experience! Can you tell me roughly how many trades you do annually and what kinds of securities? I'm doing about 300-400 trades a year, mostly stocks and some options. Also, did your specialist help you with trader tax status qualification or are you filing as an investor?

I do about 500-600 trades annually, primarily options on indices and individual stocks, with some futures contracts mixed in. My volume increased significantly over the past two years. My specialist was crucial in helping me properly document and qualify for trader tax status. They guided me through maintaining a separate trading business entity, proper record-keeping for establishing trading as my primary business activity, and documentation of my trading hours and strategy. Without their help, I likely wouldn't have met the requirements convincingly enough for the IRS standard.

100% this. Got audited 2 years ago specifically about my trading activity and trader tax status qualification. My specialist handled EVERYTHING with the IRS without charging a penny more. My buddy who went with a cheap general CPA ended up paying the CPA another $3k just to handle the audit communication. Audit protection is essential for active traders.