I highly recommend @David Greene's first book "Long-Distance Real Estate Investing" which puts action to the idea: live where you want to live, invest where the numbers make sense.I am active duty military as well, and I live in San Diego.

It also helpful to check what others are charging for pet and cleaning fees.  

Check out "Long-Distance Real Estate Investing" by David Greene.

I found one of my cleaners because I stopped and talked to her one day during a clean at a competitor's listing.

No one can seem to explain exactly who is an employee and who is an independent contractor when it comes to landlording and hiring anyone to do minor repairs, cleaning, hauling junk, etc. 

Purchase price: $52,000 Cash invested: $117,188 Fix and Flip that needed to be completely cleaned out, all new flooring, walls, bathrooms, and kitchen.

I am personally a big fan of Bronzeville and Washington Park on the Southside, both are right off the green line and are continuing to appreciate.  

Another option is just doing a clean break with the tenant.

Tenants only want a simple clean, quiet and safe place to live and swimming pools with a bunch of brats is noisy and dangerous.

@Jonathan Greene thx so much!!