Refinish what you have - flipping this property, you are going to be looking for a specific type of buyer and you will not recover the cost of residing it in a way that preserves the architectural interest of the property.

From Construction Science, Architecture, to owning Real Estate. 

@Aaron Lietz - Your post caught my attention, as someone who has taught college architecture, had two mentors, and has coached/mentor real estate in the past. 

I went to school for Architecture and after graduating went and worked in construction.

Sloped lots can also make for very interesting architecture.

Another thing we do for ranches is add a cedar lined very well sealed walk in closet in the basement for the seasonal clothing storage.Another trick we do (ranches) is add a large walk in closet as an abutment to the master b/room if architecturally feasible.

 $21K for this section (3 buildings) for the new 35 yr. architectural shingles.  

@Jason H.I’m currently an architectural designer.

After the Zoning, there are additional concerns; many of which can be resolved with good Architectural design and communication with the building department.

The boom years of manufacturing were when big parts of Dayton got built up and it was done by highly paid workers to very high (possibly unmatched) architectural standards.