I know of a great condo complex (Timberwood Villas) on the mainland that allows vacation rents with a high demand of repeat business and they start from $180k.As for Orlando, there is way to much competition from the hotels, the majority of Brits that come over only come for 2 weeks, as this is what the airlines restrict you too if you come over on a package.

It's located in a low income area; the Airline district close to the airport

I've had good luck getting deals in the suburbs of Detroit near the airport and have found excellent tenants - 100% airline employees.

That being said, I buy all my rehab materials on an airline credit card; getting tons of free miles (and pay it off asap to avoid interest)

I live on as little as possible right now and have the spare income (and methods- I churn credit cards for free airline miles) to travel, but my full time work doesn't give me the vacation time to use it!  

Work and derive your income in WA ( Vancouver)  Like many airline pilots and there is no state income tax.. then cross over to ORegon and shop with NO sales tax.. properties tax's about the same. things going for it..

It would also be nice if that card also came with other benefits such as points for hotels, airlines, gift cards, etc. 

Of course at my age I have many retired friends .. they run the gamut one of them said once he hit 70k a month without dipping into principal he quit.. my airline pilot buddies got a few million and of course if you know airline pilots a more frugal bunch does not exist they called it a day. 

There was an Allegheny Airlines plane stuck in the mud....

I'm a commercial airline pilot living in northern New Jersey and finally have the time and flexibility to devote the time and effort to getting started.