This is straight from the Chicago Association of REALTORS website:A reminder that the Chicago Residential Lease, and all of CAR’s forms and contracts, are an exclusive member benefit for use only by Chicago Association of REALTORS® members or those who are party to a transaction facilitated by a Chicago Association of REALTORS® member.

That part is working ok.

If she fails or refuses, start the eviction process.If rent is paid up and your legal tenant has some belongings in the rental, then I would probably be kind and give all parties until the end of the month to vacate, but I would not negotiate more than that.

I agree with you that it would be best to have both the company on the lease in addition to the tenant, we're just having a difficult time figuring out how to do that because of the language on our lease- It just used the word "tenant", so we're not sure how to clarify one party is financially responsible, while the other party will actually be residing there (tenant)-

-Would it be better to ask for the down payment loan and construction loan from the same party, or are there any advantages to seeking loans for renovation costs elsewhere, such as HMLs or even credit cards?

That last part is important and I realize not everyone has the flexibility to do that, but since we do it seems like an edge.

Did you run those rents through a third party system to see if they are at market?

@Logan HartleI have done a couple like this and as Greg said the hard part is guessing what your future tenant will need. (# and size of offices, bathrooms,doors, windows, floor drains, lights, truck docks).If you make an educated guess you will likely still be tearing out or changing brand new walls and concrete, but if you leave it incomplete it is harder to rent.Plan on some extra expense for those tenant improvements.

Right now I am leaning toward not replacing it since it is not broken & I have two non-bias parties saying it is fine.   

Even if you don't have a property to manage, you can start the conversation with them, explain what you're looking to do in their area, and they will be able to advise you on neighborhood insights, inspectors, and, once you have a property for them, have them go out for photos and videos.Regarding photos and videos, another option I've used is a 3rd party platform such as TaskRabbit.