You're correcting your assessment at Baldwin Park, Winter Park college Park and some of the other nicer neighborhoods in the Orlando areas are not going to cash flow due to their desirability from residential buyers.

“I’m not a sophisticated investor.”

Starting out can feel overwhelming, but you're in a great spot.

If that number is more than the value of the house at present there will be no bids (usually sometimes someone may buy it above the value for whatever reason) and the bank will effectively take the house back.

How'd I find my first deal?

If you do not have experience with that, it might be wise to approach with extreme caution or avoid altogether. 

from my advice rural properties and developments aren't successful and you are climbing an uphill battle. sounds a little niche. we focus on developing and not reinventing the wheel. if this is truly what you want to focus all your time and energy on then visit the closest 5-10 of these that look like the ones you are interested and ask if they'd expand or build a secondary one. do a lot of research before you just take action 

You are naturally smarter than most but also may be not much of an outside the box thinker. 

I'm trying to find the benefits, if any, for rehabbers but don't seem to be having much luck. 

Therefore, I set a 30-day minimum on any nights that are 30 days or more out, ensuring my calendar remains available for future mid-term stays.