You have their deposit, itemize the damage and the prorated rent (30 days) and return any of the remaining money. 

Specifically, does this use the same cap rate metrics or are other items to look at?

If you are going to commit to going through the training to become an agent, then do it full time.

The paperwork, lol, that's a functionary item and so not worth of needing some "guru", it's paperwork, I have done deals on a napkin before, literally, not ideal but hey it got the job done.

All of life is training.

These should be items like Roof, HVAC, Plumbing, Electrical, major appliances, ect.   

Obviously I’m going to be heart broken if we have to put people out on the street, but we just can’t run a housing complex with no revenue, and if you let one person slide.. when does that train end?

I work to train my clients that the biggest risk in RE investing is not an IRS audit, it's bad investments that you don't immediately dump.

Baird & Warner Im sure they have tons of great training which is so key when you are getting going.  

Your resident's renter insurance should cover their items.