Having worked from home for a long time I know the climate has changed and working from home is more common/acceptable.

If the top floor becomes climate controlled storage, is that good enough to consider the building a 4-family?

In my experience, most roofs have a fairly long life 30-35 years sometimes depending on what your climate is like.

With radical changes underway in lifestyle, wealth, climate, transportation,etc., the properties located in large, high end communities will have a much better chance of capital preservation and appreciation.

In cold climates, the expectation of a tenant opening the window, If available, when they shower is probably not realistic.  

The media template is that the market sell-off is 100% due to the coronavirus, just like all extreme weather events are the result of man-made climate change.So wait to put in an offer let another investor have it at a record low-interest rate when banks are very eager to lend money very cheap.

Anything further than that and you're more than likely going to be observing home prices from a completely different market space & climate. 

I've noticed that investors from states with arid climates don't always account for wood rot & vegetation growth.

That leads me to assume you're in a cooling climate.

The house has a pool and is located in a climate where freezing is not a concern.