To answer your question about the 203k, yes this property would qualify in this scenario as long as the residential portion of the property is larger (51% or more) than the commercial space. 

Complicated rooflines, modern details that require a bunch of steel framing, excessively large great rooms, spa-like bathrooms, etc would push you into the $1,000-2,000 range.  

You can have your own separate space with a side by side or up/down duplex. 

Perhaps a stupid question but is there a way to like parlay this into a type of themed Short term rental or vacation rental type thing? 

Being that you're an agent, you have an advantage in the real estate space. 

Put locks on each bedroom door so individual tenants have security of their personal belongings.You need a really good set of rules regarding shared common space, cleaning, kitchen use, bathroom use, etc.Be very clear about the rules up front, and selective about who you put in there.

I mentioned this to 2 agents and they looked at me like I was a space alien. 

Are buyers looking for more urban spaces, or is suburban living still on the rise?

It is very common in the investment advisor space. for example, if I find an investment advisor and want to know how his client's portfolio has performed last 3 years they do not make that  information up, its verified. 

I typically operate within the residential space and have a few rentals.