I live in Las Vegas which is a mecca for tourism, but new STRs here are very difficult to secure.

Can you just use a more common living revocable trust? 

I am very eager to start taking action and learning but live in a high cost of living market (Boston) currently and for several reasons (need to save more, move to lower cost of living place etc.) will not be able to start for at least 1.5 years. 

I think it's less of an issue of which is better and more of what are you comfortable with?

Would you all feel comfortable or is it safe to have a mortgage on the property if the value is just the land at the beginning of the build?

I give the warning because these tenants live in a little bubble and aren't considering the costs and inconvenience of moving.

On the other hand, you can make money in any area, even areas with no growth as there are still people that live there, even if the population is declining. 

The owners also still live there. 

We own 26 rentals in this market and I have lived every one of your questions in some way or another haha.

Get out of your comfort zone.