Thanks everyone for the responses, Im still going back and forth with the tenant discussing options. making sure she has explored all sources of income.On a related note: How hard is it to get a unit rented at the moment? 

The biggest challenge unique to investing out of state is not knowing the neighborhoods and buying in the wrong area.

Explore other lenders.

I am exploring the options of HVAC.

That's a very interesting situation you've got but I tend to believe anytime you can buy and hold real estate in this area (especially if that means keeping your parents in their house) then you should at least explore that option. 

I think I agree with David, a HELOC might be worth exploring if you can't get a better rate on the entire mortgage.

@Karo DarmandzhyanYou should continue to explore at the point you are at now.

I'm local to Charlotte NC and typically invest there and surrounding areas, but I'm actually starting to explore the Fayetteville market too.

Are there some unique advantages for people looking to get in the REI game in Chicago?

This will be easy if you're in a position to restructure income from your investments.My advice would be to continue to educate yourself on self-directed retirement accounts (there are a lot of traps) and whether or not the buy and hold strategy is the best option within these vehicles - my professional opinion is generally no, for a handful of reasons, but each scenario is different and requires unique analysis.Best of luck!