I could go on forever about all the mismanagement mistakes I've made on both, but the overall concept that set me free with managing both simultaneously everyday was setting my internal systems & renters/vendors work within my framework or they can go somewhere else. 

Needs wetlands and soil samples. rezoning ( what’s the zoning board basically told us it’s a done deal they’re looking for development).  

Are there smarter ways to structure this same “strong offer + liquidity recycling” concept?

Treat that first deal as your proof of concept, document the system, then rinse and repeat to build options for Thailand later.

Florida is especially illustrative of this concept because FL LLCs, especially single-member/owner LLCs, provide very little outside asset protection.

Quote from @Ashley Bitner: I just listened to an STR podcast and they were discussing an inspector - someone that comes in after your cleaning team to basically do a QC check before new guests arrive.

I have a property in MA and the vacancy is basically 0%.

Basically, don't like having new neighbors.Motion 2- Action to approve. 

So, you basically have two options:1) Find a local wholesaler that is killing it and get on their team (either for free in exchange for education or try to get hired if possible). 2) Get yourself a mentor who's actively doing wholesaling.

Make sure you understand the concept of Neighborhood/Property/Tenant Class and research it for the areas you target to invest in.