While none of us will be getting our money back he can live well selling off the remaining assets as long as they don't shut him down.

Unfortunately, of everything that you have pointed out, this would be the one I would suggest selling. 

FWIWI use tenantalert.com  They used to be different name. 

It will depend on your preferences and how well you think you will tolerate having a room mate as you approach a new life with your partner.

Rents are generally low there as well, but definitely stable.

Just Gen-Z; don't you think all Gen's might be effected by these same forces?

I would mention the damages to mitigate more however and let them know you will be doing inspections in the future because of what you found unless you are always in there anyways bc things keep breaking anyways. 

Well I was there with my antenna up, so just know that there may always be at least one in the crowd.

Lease options, and there are a variety of types of lease options, can be a good starting strategy for many aspiring investors. 

For bookkeeping it depends on your portfolio.A portfolio of 1-3 SFR's can likely be a DIY project.For 4+ you may want to consider outsourcing.For tax prep, you'll likely want to have a pro handle it regardless of the portfolio size.