Let’s collaborate and share insights...sometimes a simple conversation can spark your next big move. 

2.How can I better evaluate and communicate an investor’s return on investment (ROI)?

From simple rules like permits to outright bans so that is a huge risk IMHO.

One small tip: keep your communication channels clear and open with your property manager.

It's simple really.  

Yes both states have licensing requirements for contractors and subcontractors which can be found with a simple google search

Miami is still doing well, Fort Myers is adjusting and has lower real estate than 12 months ago, etc..)My simple thought, for what it is worth, is choose a place to live and not invest in:  choose the location you and your family WANT to live in ( because of the schools, taxes, weather, other family there, etc...) and then buy and do real estate there (and get whatever licenses you need once you start third party management).I wish you well!

Buy a few books, start simple, do your own property managing.

This could be simple as a coordination of who the debris disposal transportation will be that everyone uses, so it's 1 entity vs 40 trying to get in and out cluttering up area. 

•Tenants demand prompt, high-quality service and without caring about cost •Vendors seek to earn as much compensation for their work as possible.Balancing these needs requires thoughtful stewardship, strong communication, and a commitment to fairness.