Chicago has such a great investing community compared to most places in the US I have visited!

You could also get a couple different agents in the area to get you good comps on what to sell it for and compare on what they say the out price can be. 

A lot of properties in Cleveland are so cheap compared to Vegas that you'll think every deal is amazing.

Not in Austin TX, now it is Austin CA where you make your money on Appreciation but you have to hope the market rewards you.  

Understand the fees involved and calculate the total cost for an entire year of management so you can compare the different managers.

Quote from @Alecia Loveless: @Jorge Caceres When we have to include heat in our rent we just raise the price accordingly to the max comparable amount that other similar units are getting.

The 2nd person really liked the house and even mentioned how nice the rehab was, relative to comparables they have seen.

HUD and Agency financing is another beast compared to conventional or non-bank lending (Secondary Market).

Just don't make the mistake of comparing what someone else profits on a role, to decide whether your compensation is sufficient or not. 

I am curious though, in hindsight, how does an investment in STR in Hawaii in 2012 would compare with other markets over this period of time despite all the regulation headwinds?