@Edward Jakubiak, It's an ever shifting landscape that looks like the worst gerrymandering you'll ever see. 

Lurkers: If you are reading this post 5 years from now b/c you found it on google (or "space google" b/c it's the future), and my signature block shows that I'm a mortgage banker again, there's probably a reason, that would be a pretty good indication that the market shifted again.

The second time we went 2 days after it was posted and they already verbally accepted an offer for above asking which we were not willing to match since in our opinion it is still a buyers market in the Chicago area and based on the previous 2 years worth of data in this subdivision 10/10 homes sold below listing price, so either that buyer was an outlier or the market is shifting (Or other buyers are figuring out how good this location is).

If the hurdle is not crossed, investors get whatever property produces and you get nothing.Some sponsors pay whatever is possible and shift any unpaid balance to the next year.

Currently we are under supplied and I do not see us being over supplied unless there is a major shift in the economy.

Housing prices are fairly stable historically, and to the extent that I need to live somewhere, I might as well gain both experience and purchasing an asset while doing it. 4) In this ever-increasing technological society we live in, I might not be living in the same place for 30-years like previous generations.

I beleive, that right now seems like things are shifting in the industry and being an investor with a general contracting company as your own will put you at the top.

I believe they are getting bought out and I dont know if this is a temporary hiccup but we are really feeling that based on this we are going to start the process of jumping shift to different online software.  

And historically, the rental market doesn't shift as much as the buying/selling market.

It's a way for us to keep a similar amount of $ going into our housing but shift it from paying rent to someone else to paying ourselves for my current roommate and myself, and my girlfriend hopefully gets to keep her current house and she also gets to keep her mom close, which is an important factor to her that I won't discount.