I did last year. Had W2 for my bartending job and 1099 for DJing special events at the same venue. Made sure to document EVERYTHING for the 1099 work - kept mileage logs, receipts for equipment, music subscriptions, etc. Filed Schedule C with all those deductions. Ended up owing less than I expected! Just make sure you're setting aside money for taxes throughout the year.

Thanks for sharing your experience! That's really helpful to know it's doable without issues. Did you use any specific tax software that handled the dual arrangement well? I've been using TurboTax but wasn't sure if it would get confused with both forms from the same employer. I'll definitely start documenting my expenses better. I have some equipment purchases and mileage that should qualify for deductions. Did you pay quarterly estimated taxes on your 1099 income or just handle it all at filing time?

Thanks for the warning! Yeah, the social media stuff was definitely on their schedule - they'd just tell me to "go handle the Instagram during slow periods" of my server shift. I didn't even think about the payroll tax angle. Now I'm wondering if they're just trying to save money by putting some of my work on a 1099. Not cool.

This happened to me too! My accountant said it's actually illegal if they're controlling the work like that. I showed my boss the IRS guidelines and they fixed my classification. Saved me like $700 in self-employment taxes I shouldn't have had to pay.

Are these university programs accessible to enrolled agents, or are they mainly designed for attorneys and CPAs? I'm an EA looking to expand my knowledge but have found some programs won't admit me without the legal or accounting credentials.

Most university tax programs I've attended are absolutely open to enrolled agents. The NYU program specifically had a mix of CPAs, attorneys, and EAs. They care more about your professional involvement in tax work than your specific credentials. The only exception I've found is some specialized legal-focused tax workshops that require a JD, but those are clearly marked. For technical tax knowledge, which is what you're asking about, EAs are welcome at all the major university programs I've experienced.

I've heard of Spidell but they seem to be California-focused. Are their workshops applicable for practitioners in other states? I'm in Illinois and need resources that address both federal and midwest-specific tax issues.

That's a good point I hadn't considered. Do you know if state tax agencies are generally easier to deal with than the IRS? And do they also have programs like the Fresh Start or Offer in Compromise?

In my experience, state tax agencies can actually be easier to deal with than the IRS. The phone wait times are usually shorter, and you can often make an in-person appointment at a local office. Many states do have their own versions of settlement programs similar to the IRS Offer in Compromise, though they might call them different things. For example, California has an "Offer in Compromise" program that's similar to the IRS version, while New York calls theirs an "Offer in Settlement." The qualification requirements and terms can vary significantly by state, so definitely look into your specific state's options.

Did the attorney deal with both federal and state taxes? And how did they handle years where you didn't have documents?

Omg I didn't even think about that possibility! How would we know if that's what happened? And what did you have to do to fix it?

You can usually tell if there's potential identity theft if the notice mentions income sources your son didn't actually have. For example, if the notice shows income from employers he never worked for or investment income from accounts he doesn't own. In our case, we had to file Form 14039 (Identity Theft Affidavit) with the IRS and provide documentation proving my daughter's legitimate income. We also placed a fraud alert on her credit reports and froze her credit as a precaution. The IRS has a special department for tax-related identity theft cases, and they eventually cleared everything up - though it did take about 4 months to fully resolve.

I work in tax prep and we're definitely seeing an uptick. The IRS got a funding boost to go after unpaid taxes, but their systems are still outdated. They're basically casting a wider net with automated notices hoping to catch actual issues, but it means way more false positives.

Do you know if property management time counts toward the 750 hours? I spend about 10 hours a week managing our rentals, but I'm not sure if that's enough to qualify.

Yes, property management time absolutely counts toward the 750 hours requirement, so your 10 hours weekly would give you about 520 hours annually. However, that alone wouldn't reach the 750-hour threshold. The bigger issue is that you also need to spend more than half your total working time on real estate activities to qualify as a real estate professional. So if you have a full-time job outside of real estate (say 2,000 hours/year), your 520 hours of property management wouldn't meet the "more than half" test. This is why it's often easier for one spouse to qualify if they're primarily focused on real estate activities.

How do you determine the split between land and building value for depreciation purposes? My county tax assessment breaks it down, but I've heard that's not always the best method.