Pros and cons of an area, who lives there, what jobs do they work, are the schools good, is the commute time good, is the crime rate high, what are the rents, etc.

Anything cash flows with a big enough down payment....But if you're looking for the low /no down payment options and cashflow it's unlikely you'll find it anywhere worthwhile /reasonable distance from Travis.

I’m interested in the Chicago area and the NJ-PA-MA (as I will most likely be returning to NYC they are easy commutes). 

I have been listening to the Bigger Pockets podcasts on my hourly commute to work and have loved every episode.

Just finished reading David Greene’s book Long- Distance Real Estate Investing  , which I highly recommend. 

We are long-distance investors in Japan, investing in north of Minneapolis.

This is my first time investing in real estate so is it even worth it to make my first investment a long distance one?

to answer your question for a 7' door to work the distance above the door to the ceiling will need to be 12"-14". 

I am located in Bartow County so it would need to be commutable.

But I’d like to come back with already a few doors under my belt, kickstarting a career switch “nest”.Which kind of difficulty am I looking at to start with the first property from a distance, then to eventually have around 30 by the time I get back?