Fatal mistake to buy that on the forward curve.My recommendation would be to get out of this position; the STR is in an extremely oversaturated market and the underlying asset is a clone of many.

The general rule of thumb when using debt is to ensure that whatever asset you buy with the debt should make more than the debt service.  

Which island are you buying on?

I agree that some of these smaller towns have great buys and strong rents. 

We mostly buy houses from out of state and are aware of it's challenges but many investors have done successfully, so it can be done.

NAR considered job growth, financing, renter who plan to purchase a home, migration to these metro markets, number of renters who are planning to buy as well as homeowners who plan to move.

Learn by experience and making mistakes.One issue is most people who buying coaching only buy one program or max 2, so it's pretty hard to rank them.If you are convinced this is what you want to do, I'd look at Lifestyles, Total Wealth Academy and Brad Sumrok's programs. 

Lastly the real estate agencies and FTC and state AG's are really starting in earnest to finally crack down on Wholesaling the latest article on We BUY ugly HOUSES brought it to light in a big way..

People are buying stolen identities off facebook groups and using that info to apply as someone who has good credit and making fake paystubs.

Once I get the homeowner to sign the assignment,  do you want to be the first option to review the numbers and possibly buy ?