That brings up another issue, you can test your subs by where they use grout vs caulk.Depending on your strategy, buy right? 

The Disney/Orlando market is vast, and it's unrealistic to believe you can buy a home that is already nicely decorated with "typical" theming, in a resort area with hundreds of similar homes -- and expect exceptional performance.So how do you find/or create uniqueness in this market?

It's unbelievable that anyone could be so bad at buying real estate.

I am guessing that the agent you used to buy did not specialize in investing in the area, or they would have guided you to other options where you can legally rent short-term. 

If we buy right, how much is too much for a first timer when it comes to risk alone? 

Staying liquid and ready to move on a deal when the right one comes along is always a good approach.If you're looking at buying, I'd focus more on long-term fundamentals over short-term speculation. 

Would I buy 5 pr 6 at a time and do a lease to own?

I make money indirectly when people buy "desktop" because a few of them buy my book on desktop... but I recommend "online" because it makes it so easy to collaborate with your accountant.

@Jordan Lisnow Did you end up buying the seller financed property in Florence?

don't be afraid of better markets in ohio like columbus. depending on the capital allocation buying old houses and having to renovate is not the only way to drive value. build rent refinance repeat and build to rent are both very strong market drivers as well and you can traditionally get infill land in areas like columbus in much better locations than where you buy.