About all I would add is to meet with several pros, like an architect with experience in this area, lenders, environmental firm, for lead asbestos, etc, engineers to make sure the place is even sound, subs in all areas, etc...etc..

If done correctly (with windows, nice stone finish material, etc), it could be an architectural asset as well.With some proper professional landscaping (maybe also cut out a planter along the side of house), and addressing the driveway issues, that should eliminate the aesthetic liabilities and give you an amazing amount of curb appeal.There are other possibilities for completely redesigning the approach to the entry (straight off the front with a right-angle landing and a gabled portico), but would involve a lot more demo-ing, building, and expense.Similar to this:http://www.houzz.com/photos/17493/Becker-Architect...

The first line in my listing is prominent note about the current restrictions on STRs. 

My wife is an architect and quit her formal W2 job, and is consulting part-time with clients while also support the daily operations of the STR business.  

Designed by architect A.

Some have embraced it, some allow reluctantly, some don't allow it.Those that don't allow Checkbook Control will have lengthy and prominent marketing materials about the dangers of Checkbook Control.Those that don't allow Checkbook Control also have very fine print that explains that they (the custodians) make money on the funds that they are holding.

We can paint white for upstairs and stain mahogany downstairs.I don't think we will push the house up to the next higher Quality level, no matter what we do (Q1= unique, exceptionally high quality, architect designed, etc). 

Your architect will then design the house to make sense. 

The worst part was, the listing pointed out the original architect (who was MCM famous), but the rehabbed interior now looks just like any other traditional with no nod to the architecture at all.

Make sure you have consulted an attorney (for land use / deed restrictions, etc) and architect PRIOR to applying for permit / board review...