I'm kind of house hacking (using rental income to pay a mortgage on another house), and am interested in purchasing multiunit properties.

It all depends on what your investors are looking for.Sounds like you haven't settled on what kind of purchase you want to make.

@Calvin Lipscomb What kind of companies are you talking to in Chicago?

but also seems kind of unlikely? 

That sounds great in theory, isn't it kind of easier said than done?

This is one of those cases where you could have all kinds of lease wording texts and solid proof to make a legitimate case you were right ..but in eviction court when the judge hears you took those private photos after agreeing not they will almost assuredly side with the tenant and you will get your %^* handed to you in court

The title kind of gave the question away, but how important is air conditioning when evaluating a rental. 

You will likely pay some kind of closing costs.If you buy right and the new loan is a good loan it's worth the cost and starting the term over.

Thanks for the advise and kind words.

Hey just wondering what kind of questions you guys ask a potential realtor to kinda help screen out the ones that you feel are gonna just waste your time.