Like your lot is in down town NY. 

The first couple of things I would recommend are:Make sure the city/town where the property is doesn't have restrictions on short-term/vacation rentals?

Towns I am most interested in: Bourne (Not cape cod side; east of the canal), Wareham, Marion, Mattapoisett, Rochester, Plymouth, Halifax, Lakeville, Freetown, Acushnet, New Bedford (north end or center), Dartmouth, Westport, Fairhaven, Carver, Kingston, Plympton, Middleboro, Berkley.

@Mark Shafer, I would say also look at how long the town homes in that complex are sitting in the market before they sell and at what price: that gives you an idea of how quickly you can sell it if you needed to and at what prices.

Because that headshot looked like it could have been the twin of the guy with the same name as you, from the same town as you, that got arrested for robbing a bank.

(Long Story Alert) Some back story...This summer, I made the decision to NOT return to UCA and study medicine, but instead go to the college in my grandparents town (it is cheaper) and take classes in Finance (Real Estate) and Entrepreneurship.

Some towns like North Adams are coming from nothing on the way to nowhere. 

Also, if X location is cash flowing nicely, but everyone in the town works for one company that is a non-real estate risk that I would like to be aware of. 

There are a couple of spots in town you should avoid; however, Omaha is pretty good overall.  

Looking to begin out of town investing prior to my move to the peach state.