He will hold contracts and provide labor and material for the majority of architectural work (i.e. framing/ drywall/ flooring)I have never done this and I could use some guidance/ thoughts from those who have done something similar.

(BTW- my "day" job is doing architectural planning/ interior design for a retail chain of stores, and I design store facades all the time. 

Properties in the H-1 overlay are subject to additional regulations, mainly that any changes to building exteriors are required to be approved by the city's Board of Architectural Review. more info here https://www.lexingtonky.gov/br...

However, it really does sound like you have the hard stuff already covered between legal and architectural.

And in some locations, an addition of this level will require stamped/sealed architectural and engineering drawings.  

Does this include the engineering/architectural, utility hook up fees ect?

@Edgar Martinez Edgar have you ever traded architectural drawings for equity in a project.

Thorough research of your project’s financial and architectural design constraints will eliminate costly assumptions and guess work by uncovering facts, establishing construction costs and a realistic project budget.

These guys usually have knowledge in multiple trades and the project management skills would do more for you that knowing the difference between 3 tab and architectural shingles.

Are there approved architectural drawings with a schedule of fixtures and finishes?