Nice homes that I can only guess would be in the 1.5 - 2M range are going for $450+ a night. 

As far as repairs and maintenance if your looking for small rehab deals that price range your looking at will be very slim and if you find something in that price would most likely be in your C or D areas, with that being said back to first question are you willing to manage them or not?

Most of the time, they make you decide the pre-payment penalty based on a range of interest rates they offer.

It gives you a broad base to work from and a substantial range of knowledge when making connections.

If the equity is sufficient for the down payment and qualifying for the new property there are some excellent HELOC or even fixed rate second mortgage programs available.

I think we've answered the question sufficiently at this point.

As an example oceanfront homes STR's typically begin in the $1M+ range, and more conservative initial SFR investments begin around the $350-400k mark.

and seeking some wisdom for a rookie.Interested specifically in Kissimmee/Orlando/Davenport as Disney market feels familiar to me and it’s generally a cheaper entry point than beach condos.Looking at Regal Oaks (staying here now on vacation myself and enjoying it, though have read mixed things about occupancy), Windsor Hills, and Champions Gate.Goal is to have a second home that I AirBnb out the majority of the year but also can escape to when NYC is ruthless (like now :) hoping to live in the 150-250K range, bonus if there’s a pool (regal oaks has community pool and individual hot tubs), and solid amenities.Other than reading for my life, how can I number crunch and prepare for this?

as the neighbor would retain some value in the land (easement for drain field) and the land is essentially un-developable, what is a fair price range?  

As of now, HELOC rates typically range from 5% to 7%, but it's essential to check with multiple lenders to get the most accurate and competitive rates.Joshua Christensen - I totally agree with these points as well.