You have to put yourself out there and get out of your comfort zone. 

If they won't manage a property because of the neighborhood, then I know that is a red flag for me to avoid.4.

One of the project neighbors slowed the project by 6 months by appealing the staff decision through design review, planning and zoning and city council.

There will always be demand in the market (it's not like some covid markets that could disappear as vacation destinations almost entirely over the next decade), and the regulation risk is as near to zero as you can get in this industry so long as you buy in the approved tourist zones (again, compared to some smaller/less mature markets where they could outlaw STRs tomorrow).For short period cash flow there are better options. 

Looking at some properties around there and it seems to be the norm to have a cesspool in a few towns (WW, Coventry, NK/SK)Any immediate watchouts or gotchyas / red flags?

Quote from @Deborah Wodell: Bought a property with what we thought had a side yard full of junk and then discovered it was actually a small neighboring lot with zoning and public nuisance fines.

I had to step out of my comfort zone and walk up to them to get their attention but it helped me.

Thats a red flag.  

In my experience in foreign countries, there is often less consumer protections/ no central MLS or licensing/ greater risk to the principals, much more red tape, and overall higher transactions costs than here so it's important to look at the whole picture not just the commish %.

Certainly not afraid of it -- the government red tape is Partly a question and difficulty removing a bad tenant is probably he biggest downside - that goes for any property though.