The worst experience we've had was with a flat roofer (very common roof type in Chicago) we finally wrapped up, after waiting almost two years for them to finish/fix something. 

Maybe a new roof put on my Ralph the nighttime roofer?

To avoid the risk management/insurance that comes with tenants' wood fire use:I'm thinking to seal the chimney cap on roof and run a cord putting an electric Infrared heater fireplace in there, so they can still open the glass and get heat and watch TV over the mantle, but can't burn anything or have any flame.

Inspections--house, termite, possibly separate roof and structural8. 

The roof and gutters are only a year and a half old.

We focus on CapEX before beauty. as a realtor we understand selling or renting homes you have to make the home function, Roofing, windows, electrical and plumbing. after we address these we focused on beautify making sure the upgrades match the area and is forward thinking with color scheme, flooring, and flow.

Everything seems to work as is for the time being, but I'm budgeting for the roof and furnace replacement in the near future. 

Prices are through the roof in this current market with low inventory and single and multi family properties just don't pencil out.

My assumption is that it still will be better to purchase in my name (better loan terms, ability to put 20% or less down, and I'm already pre-approved) and move to an LLC, but this seems like a steep cost of doing business.

Metal trusses and roof.