It has had many self done additions over the years so going to take about 250K to do the remodel.When all said and done will be a mostly all new 3/3 plus 1/1 in-law suite, and two apartments 1/1 and 2/2.

Self manage. 

My guess is that a lot of mom and pop self managed properties freaked out or just decided it wasn't worth the hassle.  

I’ve been doing my research and self education for the past year and half and finally got the guts to pull the trigger.

If you buy in a nice part of Chicago it's pretty easy to self manage after you move out using services such as Cozy for rent collection (it's what I use and automates the rent collection). 

I would add a few to your list: "Atomic Habits" by James Clear, not about RE but a great self development book. 

But prices are insane out there right now and anything remotely acceptable on the MLS sells immediately.Its pretty easy to self manage.

No criminal background.He has his own electric company so he his self-employed with 6-figure annual income.

I had an in house loan for the majority of it, but being a self employed real estate agent lenders don't like to count your income very well.

Many/most of those people need that kind of structure because they lack the self-discipline necessary to use any kind of debt responsibly, and tend not to be very sophisticated when it comes to investing.