There are a lot of bad tenants so you need to screen well and buy in areas that will attract decent tenants. 

Usually, buildings that are eye-sores in the community attract attention the owners do not want because they're usually fined if the problem isn't corrected by a certain date with increases in fines the longer the problem exist.

I find that the management of my A SFRs are truly passive and easy to manage and attracts 700 credit / 100k+ income tenants who pay rent before the 1st of the month, takes great care of your property, calls you perhaps 2-4 times a year.

While I usually try to list such properties to attract maximum traffic and price …I think contract with assignment would not be a bad idea.

Not many are in good enough shape to attract a qualified buyer.

Problem #1: The Tenants Bad property managers sometimes attract bad tenants.

I fully understand that my youth/inexperience places me at an initial disadvantage, at least in terms of attracting investors, and imbues a level of doubt to any claims remotely sensational.

If I'm looking at a market like the one you're mentioning, my thoughts are that I wouldn't want to consider purchasing single family or multifamily with more than two bedrooms because I want to rule out focusing on attracting families to my rentals.

The problems that you'll have and need to learn how to resolve will help you learn to either like the crappy tenant business and look for more, similar properties, or buy properties in better areas attracting a higher quality tenant, or become a note investor.

It will depend on what type of tenants your properties attract, but assuming your properties are in PA, I can't imagine too many folks wanting to move in the winter!