I'm having difficulty finding insurance for this arrangement. 

The problem is difficulty in matching houses sold to the house I am working with (there's actually 3 houses in the same 1 mile radius).

The difficulty ins sub metering is that I don't believe that my plumbing is split by unit.

As many mentioned here, you will have difficulty coming back to the Bay Area market if your sold your only property. 

Also the distance it needs to be moved and how many traffic lights,power poles,trees,etc. there are with hills and road turns leads to difficulty.

I love the AirBNB model, I don't want money showing up in my bank account until the guest is staying - advance payments make bookkeeping really difficult (I don't want a bunch of $ coming in in Feb-March for summer reservations, then very little over summer months when the properties are actually making top dollar!)

Lots of difficulties to overcome, but I know things have been turning around.  

I hope I never have to do that but just curious as to how difficult is it.

I am having difficulty deciding whether I should sell my home and try to purchase 2 properties or use a HELOC to purchase my next place.

Even an hour adds complexity and difficulty arranging things and costs a lot in fuel and time if you self manage .