It’s a lot to keep track of, especially when researching multiple markets.Would greatly appreciate any advice/insights from experienced investors who've navigated these challenges :- How do you approach understanding and evaluating short-term rental regulations when considering a new market?

I’ve worked for some group home providers where they employ a maintenance worker who handles some of these issues (usually if the have multiple homes in a specific geographic location) and I’ve worked for homes where the handiest employee fixes things and that option doesn’t always have the best outcomes.

The sooner you use a system like this, the easier it will be to keep track of it all when you have multiple properties. 

Trying to run a successful PMC is difficult but trying to run multiple companies - VR, Annual, cleaning, and landscaping is probably going to give you an aneurism.

I am also considering multiple rentals and it appears that I have found a pretty good property manager based on feedback I have. 

I’ve done multiple cash-out refi with DSCR loans.

Cost of construction keeps going up so you need to spread out the cost over multiple units.

I hadn’t thought about the risk of expanding my portfolio by having multiple properties over leveraged, although that seems to be a growth strategy that many use,  I’m not sure it’s one I’m comfortable with.  

I also run investor retreats out of them so they serve multiple purposes.I would say that it takes a specific person who wants to invest in Costa Rica.

One of the great things about having multiple residents per property per year is that you can iterate faster than with an LTR.