Contractors performing structural, electrical, plumbing, or HVAC work are required to have the appropriate licenses issued by the City of Chicago.

That said, I’ve found that properties in C-class neighborhoods tend to perform best with Section 8 tenants.

Aaron I would not pay but if they wanted to have this added I would have a licensed electrician perform the work. 

The return on equity is probably very low considering they are paid off so maybe explore refinancing or selling the lowest performing one(s) or your biggest headaches to reinvest in more lucrative deals.I noticed you also used a metric of number of rentals to attain your goal rather than $$$/month.

In fact, someone just called me last week and had a non-performing rental package that they purchased in the same fashion and the prices they bought at, considering the actual condition and historical performance of the properties was too high in my opinion. 

Always perform thorough market research and verify the numbers on any property you consider.

I can only speak to the Texas market, where malls that focus on creating consumer experiences (coffee shops, kids play area, entertainment-based tenants) are still performing well even in this age of online shopping.  

@Randall King If you find the property isn't performing well, a 1031 exchange would defer the tax and concentrate that equity into something that has a greater cash flow potential, like what @Corby Goade said.

Permits and LLCs for Contractors:Your associates/relatives don’t necessarily need to create an LLC to perform renovations.

I’m thinking with a 2.25% rate, that’s a good mortgage to hang on to if it performs well as a rental.