I am a big believer in living in a property before going through with a non-owner occupied investment.
I purchased a single family home (4 beds, 2.5 baths, with a finished basement) in Towson, MD. I live here, and rent room by room and cover the mortgage and more.
Think of real estate as a deep pond with a ton of lily pads to jump on. Aim for a lily pad where you can safely land (and not sink). If your first jump is smooth, you'll be more willing to jump to the next, more advanced lily pad.
My first home was my baby step lily pad! Now I am a BRRRR investor on town homes in Baltimore County :)
That being said, where can you see yourself living and having roommates? I recommend a location that is within 1 mile of a public university, 1 mile of a private university, 1 mile of a hospital, and 1 mile of a major company headquarters. If you can get 2 out of those 4 you shouldn't have an issue of finding roommates who you wouldn't mind living with.
@Kelly M. can you speak to your experience with investments in the City?