It's nice to have all 4 components of making money in play for a S2 w/ wrap, but 3 out of 4 is never bad. 

Sorry for the bad picture, but you can see the alley the garage is on is about 6' above the back yard.

He can walk into a house in Baltimore and point out even the slightest details for the good and the bad.

Are they fighting with a spouse/partner/roommate and need a place to live ASAP?

If you know you want to do real estate you might be better served with a business degree of some sort (finance) as you're going to get into lots of financial analysis to determine good deals vs. bad and more. 

I really don't think this is that bad.

Biggest focus should be on a company who isnt going to rob you blind with repairs or is more interested in getting their placement fees every few months for the bad tenants they continually place. 

Growing up, I was always taught debt is bad. 

Tenants will often fight to stay in a space they know is a great value that is hard to find elsewhere.

I know turnkey can get a bad reputation but there are several reputable providers there and if you hold them long term they can be good investments.I’ve done the DIY method and so far turnkey is better for me in my opinion anyways.