And there are so many small carveouts for special interests in IRS interpretations.

@Leslie Cunningham this is such a specific niche that it might be hard to find someone that specializes in it. 

I specialize in STR'S Feel free to connect and I can cover in more detail. 

If you are a Real Estate Professional this cap does not apply and hence why it is such a powerful status for tax planning.As @John Underwood said, Schedule C income categorized by "substantial services" such as turn down services, meals prepared, or special activities provided.

Do they tend to have any special issues with vacancies, or more maintenance due to the type of renters?

Pick an area that you want to specialize in, and then work on it hard! 

Thanks for all the comments, specially about the tax exemption (that was not on my radar!). 

Special form.

Also, I'm not sure what other assets your parents own and the size of their estate, but there is a major change coming to estate tax laws in 2026, that depending on the size of their estate, gifting may be something to consider while the exemptions are high, which comes with its own sets of pros/cons.  

Some of the stricter regulations you could see include an 8% transient occupancy tax, the owner (you) having to occupy the residence for 180 days per year, reapplying every year for a provisional use permit, limiting number of occupants, and special permit fees ranging up to $500 per permit with a public hearing per permit.