But, isn't Yale University more popular since its one of the Ivy League?

I'm very cautious and definitely not in the same league as some of the investors posting on BP. 

Ithaca is like another planet.STRENGTHS-  appreciation is pretty much guaranteed, no matter how crummy your property is-  student housing isn't restricted, they'll live anywhere-  having an ivy league school means there's a lot of money flying around-  rent is high-  tons of development and growth going on-   strong STR performance outside the city properWEAKNESSES-  almost absurdly high prices-  similarly absurdly low cap rates-  pesky annual inspections required on multifamily properties-  most deals happen behind closed doors, and agents tend to be very unhelpful-  5-7% cap rates typical, sometimes lowerSummary: Ithaca is a great market to park your money in and wait.

Outside of work my interests are sports, fitness, poker and coaching my sons little league baseball team.

Sorry, I forgot, we champion those for skill of carrying our food and give out tip's left right and center to them, and for r.e. agent's we vilify them saying why can't they do it for 3 ramen packet's and a sugar cube....... 

With so little inventory and bid wars , and hundreds of showings of each property to some fake buyer who never intends to buy house, I don't think Erics in this game are in any particular disadvantage compared to "licensed" REAs (licensed is in quotation marks,  since a lot of people seem to put too much significance into obtaining it, as if it was a law degree from Ivy League school).

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?

And in coming to this point as a natural earthy mama and many years of midwives, home births, La Leche League meetings/many years of nursing my kiddos on cue.....  

Is your property in one of the resorts (Champions Gate, Storey Lake, etc) or off in a private neigbhorhood?

The ones I recognize or have talked to in the past are Champion Homes and Pratt Homes.For financing, if you want to avoid problems for potential buyers or for yourself when you refinance make sure they are "Modular" and sitting on a proper foundation.