All, I am looking for some guidance on market evaluation of a retail space in Santa Cruz County. 

For example, your second floor (and I don't think you mentioned if there is private outdoor space) is a plus that regular apartments or apt buildings won't have.

There's an extra office space that I can convert into a bedroom for myself, along with 4 other ones upstairs that I'm thinking of renting out for $800 each (1 bed 1 bath in the area is around $1300 according to rentometer).

Ask them if there are any vacant spaces in the park and what incentives would they offer if you brought your own home into the park.

Hey Jon,Since it's still residential and you're not in the commercial space (5+), treat it as the same as if it's residential - the process is the same. 

Renovating the kitchen and creating an open/modern feel in the living space of this house really puts in on a different level.

Removed a non-structural wall to open up the kitchen to the living space.

We currently are renting out a space in a local high school. 

A space that is double the size could potentially be double the cost, but just because you have double the units doesn't mean it's double the cost.  

In a space like real estate with variables, deadlines, unforeseen challenges, etc. it provides good prospective and working through those.