Coming from other areas and moving here, I've found Kentucky to be very friendly in the out skirts however my experience is limited to Lexington and Southern counties.

First, Texas is one of the most landlord friendly states in terms of laws.

We are frequent users of the Rental Property Calculator and have found a few promising leads thus far but also know that is just the beginning of the process.

But Mathew's comments above have given me pause, as most of my friends in the neighborhood that could afford the rent of a new condo have a car (or two).   

It all started when my wife's college friend offered me an opportunity to invest in a commercial property.

@Duarte MarquesPossibly but highly not recommendedFor those with no real estate experience or experience in taking on debt, it’s not easyTo do it also with little to no down payment or reserves in most occasions will end in disasterReminds me of when in high school a friend used to let his dog drive his car.

Abandon the Peurto Rico dream for now and look at more realistic/beginner friendly areas that still sport a large latin influence and strong rentals, like Florida (I've looked a little bit outside Miami..Boca Raton, Tampa, West Palm Beach, etc). 

PM me and I can get you in touchwith some Wholesalers or Investor-friendly agents around Houston :) 

I am remembering a lawyer friend advising her parents on land issues.

@Patricia Andriolo-BullStessa is an excellent platform for tracking income and expenses for investors; it is user-friendly.