There are many Chicago RE investors with no mortgages that will provide a downward pressure on rents to achieve maximum occupancy.

I heard a podcast recently where one investor would not look at apartments unless they had central heat/ air.  

What's your average life span for the following:- AC and air handler/furnace (replace both at the same time?)

The HOA won't allow weekly rentals or Air BnB style stuff which is a shame because I could rent the heck out of it for the summer and winter (it's near both lakes, mountains, Tanglewood, and a ski resort).

We once replaced the cracked single pane window in a kitchen, because that was the worst one in the apartment, and the day that it was installed the tenant asked us why we didn't replace his bedroom window first, because it was blowing cold air on his head when he slept.  

To make a long story short, she was lying about leaking skylights, air conditioners, stoves, and many other items.

@Scot Howat - Exposure of his experience is good therapy for him, and that's ok.But, as @Steve Smith said "Takes a lot of courage to post that you lost"So, as I have said before some people are comfortable about airing their failures and others are not.Our discourse will end at infinity without any wrong or right affirmation.I look forward to reading and/or commenting on your future posts.

I put the details in the google doc as its easier to display than in the posting section.https://docs.google.com/spreadsheets/d/1Gi7HweJKvb...Additional Non numbers informationThis would be my first propertyYes there are cheaper placesNo I can't buy those as they are too far from my and my fiances places of employment (this one is already on the edge)Owner Revenue is us paying ourselves our current rentWould consider this a B property in C neighborhood Each unit has central air, W/D, & Dishwasher, all of which are considered luxury items in an apartment.

I am thinking about buying a house in Austin. It will eventually be our primary residence, but, because we are in a lease situation until next year I wanted to put it on HomeAway or something similar to cover the mort...

We also have a multifamily being rehabbed in Elkton, and my wife and I separately own a townhome that we rent out in Bel Air.