A tenant doesn't qualify for a S8 voucher by making good financial and life decisions, so what quality of people do you think the system is dealing with?

In my experience, Section 8 tenants are low-quality.

They have a high hassle factor and he sold most of them.  

Do capital gains offset passive losses that the investor has, so someone really isn't paying a high capital gains tax as they thought? 

We've had clients over the years who love Bronzeville & Hyde Park and have purchased large buildings with condo quality finishes or updated the buildings & are cash flowing while living in the building.

The downer is that financing through an LLC would mean “commercial loan” which has a high interest rate of nearly 9% in today’s high rate environment.

There is no high speed internet available yet and we haven't sprung for Starlink.  

This is the class of property that I'm referring to when I talk about very high tenant demand and low vacancy. 

Review the quality of the tenant base (do they have a history of paying on time, what were the original screening criteria, do they have applications on file).

Quote from @Ana Mills: The high quotes for the electricians will be way cheaper than having your handyman do it and it causing damage, causing a fire, or even worse causing a fire later when someone is living there and that person/persons getting hurt because of the work being done by an unlicensed worker doing the work.