Is it feasible?

Rob:Five to eight years ago, I may have agreed with your sentiment, but the newer products have pushed the envelope of feasibility - there are products out there now which maintain a CoP > 2 well below 40F.  

Since we normally rehab for rental, when feasible, we will pave the drive (even overcoat/chip seal) as it makes a better surface for snow removal, etc.

I ended up deciding to work with a smaller, local brokerage that is more flexible (the KW training program is renowned but not feasible if I wanted to keep my day job, which I do, because it's much easier to access funding) and that has a history in the local multi market, and in building and development.

I know there are many experienced investors here that would vehemently steer you away from condos, but they offer a very feasible solution if you intend to purchase with cash and are on a smaller budget.I'm sure many here would disagree and would tell you to use your cash to secure a loan toward a multifamily, but it really depends on what your goals/expectations are.

How feasible (in terms of timing, getting regulatory approval, etc.) is it to either expand the property's floor plan or build 2 units on the property?  

I inquired with my financial institution about the feasibility of doing this deal so fast considering we JUST closed on our first property.

If there was a way to set yours for one-month at time (without needing to do it manually) then it may be feasible for you.

Price is $40/sq ft which seems expensive, but I am going to run an analysis anyways and see how feasible the project is. 

It may be doable, but I don't think it would end up being economically feasible, in earthquake country.