We are near a military base which I work at so I know I can rent them quickly and pretty much know I will get paid each month.condo fees are 180.00 a month there.

VA loans allow low/no down payments and are assumable and are available to members of the military. 

I am active duty military in Salt Lake City for 2 more years but my place of residence is Lindenhurst, Illinois (40 mins from Chicago).

I think the areas I was looking at were near the medical center and far west side (kind by the military base).

Military or school nearby?

"did you have any trouble qualifying for a second mortgage" We are in a slightly different situation, as my husband is military, but we are using a HELOC rather than a cash out refinance- we researched the rates and found the credit unions to be the best options....

I'm looking to get back into a military town not only for investment purposes, but to reconnect with the military community.

Since my husband is active duty military we do a lot of out of state landlording. 

By the way, my wife and I are looking into the Lansing area, I'm in the military stationed in DC but are looking to dive into somewhere in the Michigan market.

I am active duty military and as such move around a lot, and where it makes sense I buy my properties.So I have most recently moved to Albuquerque, New Mexico, and due to the flux that is going on in the military I decided it wouldn't make sense to buy another house here but rather rent.