But I think I can find a place in a neighborhood that has potential, like Central Oak Park? 

Also Germantown, Olney, West Oak Lane

@Abigail Timbol I use Angel Oak.

@Matthew Oakes a good deal always finds its way to money.

Put your chips on today's returns rather than tomorrows, since they're unlikely. 

Generally speaking, closer to Oak and Biddle are the nicest areas with access to a great little downtown.

Or should I keep doing what I’m doing now (Realtor), chipping a little bit of debt away a month at a time, but take out more debt to finance an investment?

If you have a security deposit, that's your bargaining chip.

@Jennifer Bailey i was in the neighborhood yesterday talking with some of my renters, they're college kids going to UofH, and they see no real issues. i've talked with several of the neighbors and they all seem like a close nit group trying to keep the 'riffraff' out of their part of the neighborhood(Isabella @ Live Oak). 

Lead-base paints never really bother me unless they're chipping or peeling at which point I simply prep the area scrape any loose chips from the surface while keeping the area well ventilated, clean up any debris, primer over it once that's done and cover with paint...problem solved.