If you are able to manage it yourself, I think you will get a lot of very helpful education in real estate by spending a least a year or two doing that.You'll be able to work with property managers a lot better if you've done the work yourself for a bit, and it also helps to get familiar with the various laws and regulations you have to comply with as the owner, even if you do have a property manager in place (e.g., the new RI rental registry and associated lead paint inspections/certificates).It's up to you whether you're able to do it, but I think you'll get a lot out of the experience if you can try it for a year or two.

You also need to consider any STR regulations.

This is a highly regulated activity by the CFPB.

., the specific procedures laid out by the SEC in Regulation D.  

And the locals in Highlands have been fiercely debating STR's and regulations for the last few years, so I wouldn't be comfortable buying there.

If you control how they perform tasks, set their hours, or provide tools, they should likely be a W-2 employee, requiring you to withhold taxes and comply with payroll regulations.

I saw an example recently in Bloomberg about how local regulations can really shape a landlord’s experience, from what I’ve heard.

A tax advisor specializing in real estate can help you navigate deductions, plan for 1031 exchanges, and ensure compliance with ever-changing regulations.

A break even into a profit, and a profit into a windfall. 3- Capital - I used to state this as access to capital, back when the rules were loser, the regulations less onerous, and information less readily available.

Regulations in Nashville allow owner occupied STRs if you are truly an owner occupant.