(quantity over quality kinda thing) 5.

Chicago is so vast and diverse that 400k can get you a tiny condo in one neighborhood and a 12 unit in another. 

I think an irrevocable trust would only work if I were a family member (and could receive the property through an exclusionary transfer, which wouldn't trigger a reassessment) Yeah, the property could be worth more, although the lot is tiny....36 by 45 feet, and no onsite parking or even a yard to speak of.

There are a lot of property managers (quantity) but not a lot of property managers who do a good job (quality).

Even with a decent sized portfolio at 62 units I only need a tiny fraction of the population to be good people who want to rent my apartments. 

It's basically a tiny version of a central HVAC placed in various rooms. 

The way I am seeing maximize cash flow is a cheap vacant lot improve it landscape it and put on tiny homes!

The cost of housing and living is tiny compared to our neighbors.

Since 1996 I have followed through on my personal commitment to represent the best interests of my clients throughout their real estate transactions, and after the closing.Today, success is determined on experience, and the ability to discern the relevant quality of a huge quantity of current information sources.

However I'm not sure the demand is there yet for houses in this category to be rapidly converted or redeveloped in large quantity,  but I am sure it will happen at some increased rate.Just because ALL of SFR now allows this,   it will tend to spread out the activity more,  as opposed to upzoning smaller areas, concentrating redevelopment in those areas and rapidly changing them.