My answer would certainly be highly dependent on his own emotional make up, his desire to relax and travel, his willingness to delegate and outsource, etc.

The sellers had put so much pots, plants, planters and shrubs out that I thought there were too many plants/planters that would require a new owner to upkeep.After a few potential buyer tours/showings, the owner heard all the comments (via the security cameras) about how there was a "lot going on with the plants and stuff out front".

The area has certain advantages like shelter from regulation risk (pretty much as low as anywhere in the country if you buy in the approved STR tourist zones) and long term security (people aren't going to stop going to Orlando anytime soon). 

@Chris Seveney @Nathan Gesner The owners offered to cancel their lease and return their security deposit in full.

Consider all the things that could go wrong and see if the lease addresses them: unauthorized pets or tenants, early termination, security deposit, lease violations, late rent, eviction, lawn maintenance, parking, etc.5.

It may feel cumbersome, but their diligence reflects the level of security and service you can expect once onboarded.

There really isn't a safe, secure way for someone to protect their interests.

What strategies do you recommend for securing hard money loans for spec builds?

Ask for higher security in person have them back out on their own if they still want the place you will be safer with more security

I like that you can setup different virtual accounts for security deposit let's say, or to separately ledger cash collected through a rent to own contract.