IDEM doesn't regulate heat fuel tanks for residential use if it's small.

Take this with a grain of salt as I’m not an attorney, but I do work for a large SEC regulated investment firm (~$11 Bln AUM).

Vacation rentals in proven vacation markets (read: not metro markets with volatile STR regulations) allowed me to scale faster than I would have using solely LTR income.

As mentioned before all islands have different rules and regulations on short term rentals.

Is there anything you could do to avoid a hostile environment?

1) It’s a passion. 2) it allowed me to leave my full time job that I wasn’t very happy in. 3) I’ve got flexibility in my work so that I can spend time with my two young daughters. 4) it’s going to help my husband retire early as well. 5) we provide a safe living environment to our tenants.

Let me know if you have any specific questions about str rules and regulations or finding a multi. 

The only issue we've run into is that before STRs were regulated in our city, the competition was so heavy that nightly rates were depressed to the point that they frequently fell below LTR rates. 

Case 2: I want to maximize my yield and build wealth as rapidly as I can, without taking crazy risk: In this case, you can refinance the properties, likely pulling out $100K+, and use that as the down payment on multiple additional properties, or larger multifamily properties in your area.This would increaese the effects of leverage on the portfolio (compounding returns positively in a growing economy and negatively in a recessionary environment), but over time be highly likely to build more wealth, faster, with some added stress and the need to more closely  manage operations in a much larger business that in initial years likely won't produce as much cash flow. 

@Garett Biondo I would ask myself if it’s the type of work, the boss, or the environment that makes me unhappy.I wouldn’t bail on your current path until you’ve tried a different position in your company with a different boss, or a new company altogether.