We have visibility that we will be staying in this area for at least the next 7 years.Background:We both work in techWe have about 500k invested in stock (not including 401k)We have about 100k in cash equivalentsWe earn a combined income of 550k annually include cash and RSUsWe have no kids and don't have plans for any for the next three years at least.

Has anyone found a combined app?

To prevent this from happening I combine the payments and lease signing in one visit.  

Combine that with tenants that don't take care of the place and have high turn over and the numbers just can't work.

This is combined with money coming in over time (over the term) of the contract and ideally, it covers more than anything they pay out monthly if they have a loan. 

We are nearing the end of DIY renovations ( it looks pretty awesome though and functions).

So you can imagine how inefficient the search function is for me right now.

Then for rentals, you would want some durability to go with affordability, so look up,  via the search function, the threads on how to harden a rental for ideas in that aspect. 

The inspection may allow you to spot major issues (like a hole in a tank), but functional testing can likely only occur when folks are living in the house.

The south side of Chicago is a very large geographically (South side is as large as the north and west sides combined) so it is unlikely that one property management company will cover the whole south side.