Automating housing design isn't good architecture, and that's something that's already sorely missing from our communities.

Don't forget architecture, financing, holding costs, selling costs like transfer tax and realtor commissions if you're flipping. 

I realize that submitting two sets of plans is thousands of dollars extra in architectural and permitting fees, but if I could be completely framed out and mostly complete with mechanical, electrical, plumbing, etc. by the time the parking zoning hearing/approval occurs, then it would be worth it.Anyone heard of someone doing this?

You would need to get an Agreement in place with the landowner & then have monies for the soft costs of legal, architecture, engineering.  

The Architecture, historic district tax advantages, purchase price and projected profit.

Beautiful, clean, safe, easy to navigate, great food, great architecture, friendly people.....yes...really.

Let them tell you whats needed and work with them through the process, establishing that you respect their authority on the matter and are trying to work with them can go a long way in making your life easier.For reference, a simplified lift of drawings required for a typical house permit in my area are:- a site plan, - floor plans for every level calling out life safety elements, dimensions, etc- building and wall sections describing the construction of all the building components as well as their r values - building elevations - Architectural details - Structural drawings and details- Structural Calculations  Hope that helps, feel free to reach out with any other specific questions you might have.

Worked in architecture for 18+ years on a broad array of project types: from large-scale university science buildings, museums and hotels, down to small house renovations.

I've talked with several people now, explaining the vagaries of Victorian architecture, and gone so far as to send them some 1889 blueprints of my house to explain that it's just a big house with a third floor.

And is the deal goes through, I guarantee them the contract on the architectural side.