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. 

As an example, the highest designation (MPM-Master Property Manager which I have) means that you have to have practical experience (you need 500 unit years- meaning if you managed 100 units, it would take you a minimum of 5 years), education (24 hours minimum of formal classes- or 3 days for this designation) as well as letters of recommendation from clients as well as peers (other MPMs) and you have to invest time in the property management organization be it locally, state-wide or nationally over YEARS.So the designation process, including those that are in their candidacy, takes a lot of effort and you grow through the process in many ways including wisdom (a lot actually)!