Brick facades last a very long time & foundations are very strong as well. 

The second question is, what are the risks associated with this type of installation, where the vinyl siding is installed as a sort of facade on the home?

Also, you can NOT EVER demolish any structure (or even a portion of a structure) that is considered historic no matter how dilapidated it is unless you intend to re-build it exactly as it was (especially facades). 

I like the way it looks now, the smooth tans, the overgrown shade trees, the modern facade, and a three car garage, it looks rentable and peaceful (a nice HOME vs a house).I did a mockup for you, mainly focusing on a varnished gate, varnished front doors, less mature plantings and getting rid of the big dirty (sap dripping) pine tree over the left driveway (so it would not drip sap onto the new BMW=7 Series in the pic).These kind of things would fit in, in an upscale area, but not necessarily be better, just different.It looks like a nice house for entertaining, lots of parking. 

It's the plan hinted at last summer, when a "potential developer" sunk $300K into stabilizing the brick-dropping facade. 3. the new home of the Detroit Red Wings is expected to be built and open in time for the team's 2017 season opener.It only gets better from here people.

The first year I performed a tremendous build-out; new plumbing, electric, facade improvement, new entrance for separate floor in building etc.

Adding to the façade was the attempted argument he was providing "affordable" housing... for 5 units that were easily 650K a piece.  

Invested $15,000 into paint, facade and some repairs. 

(I am envisioning converting an auto-garage with 4 bay doors into 4 stores with a new facade)During the rehab I would be using the space for my own personal projects so the holding costs would not be a total waste.

Following completion of phase 1 improvements, will update exterior facade and windows.