would love to see if we can work together, I use a couple of PML but always open to adding more to the roster

That just has been a go to added coverage here for my clients.  

@Kristian Sexton@Sami Gren she hit it on the head. it is more of a liability issue when it comes to adding someone into the middle of a lease term.

@Jennie Berger gave you the whole kit & caboodle on Chicago zoning so I don't have a ton to ad, however, I'd highly encourage you to engage an architect like @Samuel Pavlovcik or @Prashanth Mahakali, both are awesome local Chicago resources.

This is also accounting for my increase in insurance costs due to adding insurance to the ADU. 

Jessica, we do have thousands of organic likes on Facebook and have been in business since 2007, please Google us, we are no allowed to ad links nor phone numbers on here. 

What is the main hang-up with financing, when it comes to adding bedrooms?

As @Lucas Martinez mentioned, FMV rents in Santa Barbara have exploded, I'm trying to be considerate of my tenants while also exploring a path to adding value to the investment--which I know probably falls into the oxymoron category.

Definitely open to adding value any way that i can

I would ask, what's the upside to adding him to the lease at this point?