It was clear from the video that this new law attempts to prevent wholesaling entirely, and Pickren feels that the interpretation of the law is sufficiently wide enough that any marketing for the assignment of a contract will fall of under the definition of this law. 

Aloha,Over the years I have worked with a pretty wide variety of Owners, large and small.

Your questions cover a wide territory.

I wish I had better news for you, but it is a wide spread problem from my experience.  

For example every week I see listings with bedrooms less than 7' wide.

We are trying to fill in a rather wide wealth gap

I've searched far and wide for cash flow positive multis in hoboken and JC, and have yet to find a cash flowing property (my goal wasn't to cashflow but to net my monthlies as close to 0 as possible).

I found the renovations costs to vary widely and a couple of contractors said it costs X amount of dollars with no line item estimates (red flag there).

. - I am all for a city-wide Chicago ADU ordinance. 

Not hairline crack but a continuous crack probably about 7-8 feet long and wide enough to put a credit card into the crack.