You'll get a feel for the age of the neighborhoods, the vitality of the commercial buildings, the ease of location, the closeness to jobs.The markets you're describing are more linear, and usually have lower capital appreciation.

This could help secure a higher LTV while you build STR rental history.

Also, the ability to find good deals with an accurate budget to complete the project up front from some good project managers/general contractors.

That will allow you to build the additional legal space further amplifying the value of the proprety (more HELOC money). 

It will be great to build out community.

Once you decide on a contractor I would keep the fire marshall in the loop as to the scope of work and the timeframe for completion. 

I was on island earlier in the month for an eviction trial and stayed at the Waikiki Banyan for a few nights - that seems to be a popular STR building.

It's actually the best strategy in the Nashville area if you can build an HPR yourself and own both, STR the other side. 

Go to BUILD YOUR TEAM at the top of the screen and look for local investors or meetups in your area.

Quote from @Fernando NA: Hello everyone,I’m considering purchasing a piece of land near Divide, CO, to build a small off-grid log cabin and list it on Airbnb or similar platforms.For those of you who live in the area or have experience with this, I have a few questions:>Is it possible to list such a property on Airbnb given the local regulations?