You are perfectly legal and right to do so.

Southwest Florida is definitely an exciting (but competitive) market, so props to you for diving in!

Bigger Pockets is a great place to learn and connect with fellow investors.If you’re looking to invest long distance, I definitely recommend building your core-4 team.

Unless a property has a non-conforming use permit (NUC), there are only 4 areas on O'ahu that you can legally do STRS.  

I will definitely look into this further. 

This extra road frontage now also qualifies my property to be able to be legally converted into a triplex from a duplex.

It is definitely the norm.

The issue I see with your $500 allowance is that in some seasons they will definitely be seeing a big cost.

Do not rely on it for legal advice.

I don't necessarily need the standard features of pm software, such as rent collection, bookkeeping and maintenance requests, though that could help; but do need a clearinghouse of important information, such as leases, legal docs and other information; maintenance vendors I use; maintenance history; and some kind of tracking system, where I can record the various current projects I'm working on within the business.