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?

There is variance in markets but I believe most high price markets are like my market with 2 primary plays 1) patience.

If I was here things would have played out different.  

Hey all,Any local agents or members in the area that can give insight of Fairfax county as a whole or specifically Oakton area as a MTR play?

Since no one else has chimed in on this I will play advocatus diaboli here since it’s a topic I feel strongly about.

I'm gonna play a small hand and see if I can get a counter offer accepted for the 2 empty lots next to my personal home.

Like Daniel mentioned, amenities could play a big role even if the price is a bit higher.

Find yourself a good local housekeeper, treat them well with the occasional bonus and they will be your eyes and ears. 

Given the equity you’ve got, a cash-out refinance might be a smart play.

Play chess, not checkers.