Disney is celebrating its 50 year anniversary, new sections of the theme parks are opening and International travel is not even up to speed yet..so the future looks bright.

On a residential street with families, you have STR guests speeding down the road, without regard for where kids may live and play.

If not is the area attractive to quality tenants that will pay market rents?

I also know that the lower prices to be found in NY have a lot to do with there being older buildings, higher property taxes, tougher neighborhoods, less appreciation, etc. which I know I will need to incorporate into deal analysis accordingly and understand the risk of.Summary: I feel that with having to put 20% down (FHA loan house-hacking is pretty much out of the question in NYC due to the astronomical prices here), buying a property in New York may be more attainable with my current savings and would allow me easier access to visit the property, however I don't think I could afford the quality of property I would like (close-ish to turnkey) in Florida.

Thanks for the quality post!

There are really very few of quality on market.

What do you use to keep engaged with your network and keep them up to speed on what you're up to and vice versa?

This will provide quite a few years of stable connectivity throughout the property even if internet speeds drastically increase (unlikely).

If you are able to I would find a mentor as well and this will ultimately help speed up the process of learning. 

For single family I agree that adding bedrooms and then renting by the room or using as a VRBO would be the move, but as James pointed out those would be at odds with each other due to location and quality of property (short term renters will be a lot pickier than some college students, as you'd expect).