I see dark areas on the walls and am thinking "mold".

No one, especially the ladies, likes going into a dark and dingy basement.Put LED lights in interior fixtures.  

In addition to having some extra money at the end of college, he learned how to take care of a house and although he is not pursuing real estate investment now, he is more prepared than most.I am currently in a similar situation (graduate student with a minimal stipend).

Plus, if you try to escalate rent too much on an existing tenant, you stand a good chance of losing that tenant...a good thing if you're trying to get rid of them, but bad if they are a great tenant.In the last 24-months property prices have done nothing but increase, driven by both a recouping of the lost appreciation from the dark days between 2008 - 2012 and an overall lack of inventory.  

A few reasons I don't like the listing you linked to (or similar properties):Neighborhood is rough (I wouldn't want to be there after dark)Leases in that area tend to be month to month (high turnover)Security deposits++ likely eaten up with each tenant turnover Requires property manager (don't want to deal with that tenant profile, even if I had the time)IMO this is a D property due to the location and tenant profile it will attract, and I prefer A and B properties. 

My idea was to buy and hold the 2 properties by paying extra on principal on one and the very minimal on the other.

Is it the best option when you have very minimal to come out of pocket?

My investor (family member) is very anxious to get in and out of this property quickly and wants me to do the absolute minimal possible and throw it back on the market.

In my experience they've put rubber socks over the meter leads and put it back in place, which is minimal protection from the situation above.

In order to be successful in this realm....the key is MANAGEMENT. there are very specific ways things must be done in order to maximize return while minimizing headache.