He became a contractor, worked hard, and grew a successful business that produced a lot of money.

i had a lot of success with direct mail and actually a fair amount with email. 

There are a lot of retirees there.

I know some good people that have went to dinner, had a couple of drinks, drove home, and got pulled over.

If you can sit on the sidelines and be choosy this requirement is fine, but you are going to have to kiss a lot of frogs before you find someone with that much cash on a wrap sale transaction...it may take 6+ months unless you advertise like a mad man3.

Its a lot of money to put into someone who's new to their life or the industry.

Hey @Jonathan Sanchez, a lot will depend on your area.If you are buying in a saturated area with lots of competition, then using an aggregator like Pricelabs to help make your pricing accurate is handy.If you are in an area that has less, then simply looking at nearby properties that are similar to yours on VRBO and AirBNB.

We don't have kids (might in the future), my husband and I are young and healthy, have stable high-income full-time jobs, and just put in a lot of work to both properties so don't expect huge expenses in the near future.

Based in Tampa, I have a lot of knowledge in Pinellas County rules and regulations as well as best practices/highest returns. 

Sees a lot of off market stuff because he is a property manager as well.The toughest part about investing outside of your locality is finding boots on the ground that you can trust.