Seth, for starters, good work.

Going skydiving on Saturday! 

I did pay asking price, however, this property was not on MLS and was one of those "my realtor knew another realtor" type of deals and they knew it would be a great "starter property" for me.  

I would suggest focusing on lead generation for starters.  

There's maintenance and management/being on=call all the time for starters. 

It sounds like you are heading in the right direction and there are some good arguments for both of your options above.Of course I am a little biased for the Indianapolis market and see lots of out of State buyers here do very well [and a few that loose everything due to a bad or no team on the ground].If you do look out of State, I would suggest sticking with SFH for starters [they are much less of a head ache to manage and very easy to sell later].

In my capacity as a Loan Officer and a Pro-Bigger Pockets member, I personally have gotten a chance to meet and help many people around the country with their residential and commercial loans; I am confident you will have the same opportunity to meet new people and network with like minded people.For starters, I suggest that you look around for meetups in your area, here is the link https://www.biggerpockets.com/forums/521-events-and-happeningsAside from a ton of literature this community also offers a ton of free podcasts that have been extremely helpful and educational.

Would buying a affordable starter home and renting it down the road make more sense in Baltimore?

Check out  LegalZoom for starters.

While this is more so for some people than for others, I think that bar a few extreme-self-starters everyone can use a little accountability.