This would be tons of work for a little return.

My preference is to partner on C+ or B apartment buildings. 

You do not bet on the home team simply because it is the home team. 

Portland is gearing up to crack down on STRs, so I wouldn't bet on that plan for the long term.

If you own in c or lower sometimes the tenants will tear things up.

I've worked with this population in the past and the majority live in C or D class neighborhoods.

I would run the other way, my guess is its a C or D neighborhood (without actually knowing where you are), its probably a place for only seasoned investors.I used to work for a utility that covered northern Indiana including Gary Indiana. 

Is it a C or D class property?

Is it rude if we start a pool to bet on the eviction date?

Overall, you might make more money than a C or B neighborhood, but not always after all things considered over a long enough timeline.