I think of them sort of like really big HOAs.To get a sense of what regulation looks like at a local level as it's being crafted, you can watch videos of the town of Shandaken designing STR regulations online (they put them on Youtube I believe).

Check out wholesale hotline on YouTube and also watch any of Jamil, Brent or Pace's content

Someone mentioned Hector Garcia above, and I’ve watched a few of his videos.

Sometimes I find this a bit inconvenient because she works 8-5 and I usually have free time during the day to do house chores (I'm a student) but in the evening I have other things to do, and I somehow have to adjust this according to her work time.When she's not on calls, she watches tiktok or talking to friends on her phone with loud speaker to the point that I cannot take a nap in the afternoon (my room is next to the kitchen).

I intend to buy a vacation home in Tuscany some day and love watching the market.

If this HOA is only 10 homes, I encourage you to be directly involved with them - you will have 1/10th of the vote - get on the board and watch out for your investment.

I imagine pros would be having some sort of proof that the tenant damaged the place under their watch and having some sort of recourse for it.

What should I watch out for?

do a title search, do a probate search on all interested parties, watch out for federal tax liens and bankruptcies.

You have to watch new tenants moving in because they might have stiffed the old landlord and that's how they saved up first months rent and security deposit.