The current state is that we have an architect site/plot plan and need to engage the the County to get approval. 

Hint: look for a solar architect, who acts as an adviser and works for you and audits the installer project proposal.Many states/utilities are no longer allowing net metering (kWh for kWh) and use instead all kinds of payback schemes (e.g. if you over-produce, they will gladly take your kWh for 3 cents and graciously allow you to take it back at night for 22cents - end result being, if your system is not properly sized, you will be producing energy for the utility and never recover the costs of the installation).

Looking for Architect/Builder experienced turning older 4000 square ft home into Apartment and/or ideas from people who have done this before.

Quote from @Sami Gren: HI,I am using a contractor for a full apt gut rehab, I would like to know if anyone has a contractor's contract that I can work off (of course will add or take off accordingly) he is a new contractor, so he doesn't have one,  [I am using him because I have used him for past several years on smaller projects, so I know to trust him.]Thank you A contractor is supposed to be well versed with writing contracts, hence "contractor"AIA (American Institute of Architects) has some good resources.A good tradesmen doesn't always make a good contractor. 

Your background is super impressive...agent, investor, and architect...I'd love to connect to see how we might be able to work together!

If you're just looking for a site plan and rendering I would contact a local architect.

I did talk to an architect, and he said he could do a preliminary drawing, that would give me enough to go to individual contractors for budget pricing .

We have invested a considerable amount already into the to-be-built plans, architects, engineers, etc.

The height of each unit is about 8ft I believe.let me look up the sqft I believe it's a standard sized lot for chicago so about 3000 sqft Neighborhood is starting to see some nicer units rents are all higher but it's leans more low income I have a contact that is going to ask the alderman if I could build a separate unit and have the original as an adu architect suggested extending it as they believe it would be easier to get approval than a separate home

Lawyer has been paid, Architect already has a down payment in which he created some plans already.