Less fun and takes more time, but I would suggest before you start on your own, is to go work for any builder in the area. 

Cockroaches were on fun to get rid of either.

Hey Sigmund,This is a fun question.

Will cut down trees and poison over the winter. 

Real Estate is always a fun topic! 

From there I can expand and continue to invest or pivot to hiring out agent stuff, and start having fun with investments. 

@Jesse Herndon that sounds like fun and an interesting idea.

It isn't fun. 

One of my cabin's is up on a knob off a mountain in the Smokies so different environment than you but the issues are probably the same and they all revolve around winter, albeit I am guessing yours will be much worse than ours.Mild scenario is where guest are at the cabin and a snow/ice storm hits while they are at the cabin.  

I think if you can find a $300k house that's a 3x2 that needs a little bit of work and you can have some small equity built up day 1 that might work.I would look in the Apopka, Forest City, Longwood, Casselberry, and Winter Springs areas and try to find a house for around $300k, the rent should be $1700-$2,200 and that might cash flow you a little bit.