From what I observed, the community is very tight & close, everyone knows eachother, and they hold lots of community events.

This of course is municipality specific but that's the general theme I observe.  

Just a few more game room observations.

If people want to hire you & your group is there a retainer fee that's immeadiately set up, then a fee per deal at a fixed % of the transaction.

Even after meeting their demands, they still find ways to nickel-and-dime you, such as charging exorbitant fees for retaining property photos.To add insult to injury, their customer service is subpar.

Consider converting one property into an STR while retaining the others as LTRs to establish a stable income base, taking into account your willingness to manage STR responsibilities, local regulations, and financial projections for each property scenario.

I'm not a huge fan of the 3 way split - if the current owner is going to retain the properties, but you are going to rehab and manage them, and then you have another person fronting the money to fix them up.  

And, if the home has, at minimum, retained its value then 8 years in loan payments should have reduced the debt therefore creating a potential profit when sold. 

I’ve gotten multiple quotes for retaining wall and driveway replacement.

It seems like you observed your friend making out with it, its easy, so you will do the same.