@Jennie Berger gave you the whole kit & caboodle on Chicago zoning so I don't have a ton to ad, however, I'd highly encourage you to engage an architect like @Samuel Pavlovcik or @Prashanth Mahakali, both are awesome local Chicago resources.

Owned and wholesale residential for the last 5 years, but this is a whole new game to me.

Someone messaged me months ago and told me to quit spilling the beans on the whole build and to wait until it’s done/sold before I discuss anymore numbers.

Staying flexible and partnering with a skilled property manager or agent would be key to achieving long-term success.Good luck!

@Jaren Taylor, not sure if this is why you talk about raising all cash, but given most deals are trading in the 5% cap rate range, and agency debt is 6.5% while balance sheet debt is closer to 7%, I whole heartedly agree that all cash is the ideal capital structure for many properties today, if your goal is to maximize overall returns for your investors.  

The whole thing is not beginner friendly….  

This is really an object of my hindrance to achieving my end.

{ARMS are a different beast again}) to achieve anything beyond a token reduction in interest paid.  

My client would have been willing to pay up to the whole listed price because the property will be worth ~$525k ARV. 

we just managed to get ong to run all new lines and separate meters for our whole apartment complex at no cost to us.