For markets that are completely unregulated it is a concern that in the future they ban STR and you get shut down.

I'm looking to optimize more for CAC vs. appreciation for the first few pieces in the portfolio, interested in some of the other peoples strategies in the area. 

And of course, your homeowners should already be through a company like Proper Insurance.You cannot advertise a direct booking site in any way, shape, or form on Airbnb/VRBO unless you want to get banned from the OTA.

Ensure you have a plan B, an exit strategy.

Finally the two non paying tenants leave, which the PM couldn't control either way due to eviction bans.

New York banned smoking in restaurants 20 years ago and every other apartment hasn't allowed this for years.

Some can't ban STRs, while others were grandfathered in. 

I go so far as to ban smoking outside as well.  

For these reasons, it's safe to say that short-term rentals are neither gonna be banned nor heavily regulated.When it comes to the decision between buying new build and resales, it is important to understand that properties that are considered too old are much less popular in Latin America.

- make sure weekly rentals are legal in the area you are considering - many towns are banning them or putting on a 30 day minimum. - get specific vacation rental insurance, otherwise a claim could be denied - try CBIZ - we have seasonal lake and mountain rentals (summer is peak).