My now-brokerage (Jones Chance & Co. in Ypsilanti, MI) specializes in helping people make wise investment decisions.

I am Houston based full-time Investor-Realtor (Investor-Agent) and Buy & Hold Investor, I specialized in Single-Family Homes (SFH) and Multi-Family Properties and I am very passionate about helping investors and agents succeed. 

I recently started reading “The Book on Rental Property Investing” and started becoming very interested in real estate , with special interest in Flipping Houses and Rental Properties.

Specialized contractors are best rather than hiring one contractor to do everything. 

That is what I specialize in and I would be happy to talk about it with you. 

However, I found there is a city special assessment of $7400.

I'm from Springfield, and I know a bunch of realtors but none who specialize in rentals.

Instead of ruing the extra work that Section 8 now entails, you might instead train one or two employees (if you have employees) to specialize in Section 8, then market that service to other LLs in Colorado that have the same gripes as you but don't want to put in the legwork to make it work.

There can be attorney’s fees and/or special assessments that might fall in that window.

As you said, most banks expect it and some even require a special purpose entity be created for the purpose of holding the real estate securing the loan.