It looks like due to major vote and coincidence, I should start with "What every real estate investor needs to know about cash flow" I'll then branch of to some of the books that @Giovanni Isaksen has mentioned and take it from there.

This island is known for its Sport Fishing tournaments that people come from all over for.

I don't mess with major structural issues/foundation problems, just cosmetic stuff so the rehab budget stays low.

You sail you know nothing about repairing a home so you're probably going to have to hire a contractor to do the majority of the work so getting some bids is the first step.

But, I did purchase this property and did a major renovation on all 9 units.

Something small, no major work, tenant-occupied, etc and have found 2 properties that interest me.

The building is facing a big street, near major intersection.

There can be valid reasons to do this and affordability is a major concern as if this is misused it will be seen as predatory lending.

For someone leaving a job with benefits, the realities of paying for healthcare often come as a major shock.

He's an amazing guy, and he might be able to help you out since his investing relies on being close to major transportation hubs - especially NYC feeders.