"If I were a betting man," I'd suspect that as soon as you refuse to pay the "finders fee," she'd figure out a way to get the deal signed. 

If I had to make bets I'd say it'll happen next week.

They may have had a negative experience or feel that way because of something, but everyone is different and the more money you can bring in under one roof the better hence why I believe that MFR especially the smaller units are your best bet.

I think the neighborhoods close to transit will be slightly more resilient that those further away, since you will be betting on the Bay Area (and access to SF) rather than Oakland remaining hot in its own right.  

Well that is my bet on St.

With a good chunk of your own money in the deal, I'm willing to bet you will find a partner.  

Insurance is one of the most important aspects of starting up a short-term rental, and it's one of the most overlooked issues.In my experience, it's almost a sure bet that your normal insurance carrier will NOT cover you for any claim arising out of an Airbnb-style short-term rental.

I would bet your plumbing and electric would be questionable unless someone recently updated. 

Your best bet there is appreciation and having someone pay off your mortgage for you in 15 years.

Odds are if they are asking for minimums, restricting long-term occupancy, etc. it's for a reason.