Or better yet, are you prepared to buy with a negative carry where that negative carry can grow in magnitude?

I value what you are offering; but I'm not prepared to pay $2000+$250/mth right now and go through this again. 

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?

Prepare to be mesmerized as you indulge in the opulence.

Really good job of preparing to be able to make some financials moves to enable independence.My comments are slightly different from everyone else

After cooling down, I thought about it and decided to share the experience with others so that collectively we are better prepared to address these types of responses and determine how best to respond to them. 

In my case, I was several thousand below what I was prepared to pay so I sucked it up. 

@Jayden Gales- thanks ..if you havent already done so - get  formally pre approved with a lender that offers the programs you are considering ...getting pre approved  will help you become educated / prepared  for the next step .

The kitchen is supposed to serve as an area to prepare food, but in making it part of the rest of the house it becomes necessary to make it aesthetically pleasing, which not only makes it expensive but also tends to impair its function.

I've prepared for this mentally but it still doesn't prepare you for the reality of losing the money.