Do whatever everyone else in your area isn't. 

maybe a multifamily property in a better cash flow market or be a passive investor on someone else deal 

Anyone else run into this issue?

Maybe someone else on here can give you better advice.

Etc....... there are about 10 duplex’s before mine and they are all alike (townhouse kind of styled)....MY duplex starts the next set and there are about 10 of ours as well (side by side styled) across the street and the rest of the neighborhood are alllllllll single family homes that are pretty nice and well maintained.So I recently cut down a pine tree from my front yard that I felt like was just a hassle due to the pines that it dropped leaving a constant mess...I bought a Japanese maple tree to put in place of where the pine was and some small shrubs to fill the middle of the duplex and the sides.....The duplexes I mentioned that were BEFORE me all have small trees alike and all are maintained by some landscaping company and from mines down all pretty much have PINE trees.

I would like to do it in the Chicago area (more-so the Southside where I’m from) or else the surrounding suburbs.I am in the process of currently refinancing my student loans to lower the interest rate.

You can't really access much else on the mls without an agent. 

What else should I be considering?

You still have someone else paying at least a portion of your mortgage for you. 

Your right, I could go else where.