I do also work an admin role though for the agency group and do make a fixed monthly income.

How much capital will each partner put into the partnership, how will the partnership equity be split, what roles does each partner play?

To try to help him, I want to take over the "business" aspects, and have his role as more of a project manager, essentially overseeing the day to day operations. 

I think it comes down to spending the time to interview several people (or more) for each role (realtor, property management, inspector, lender etc.) and not being afraid to keep asking around if one doesn't fit your needs.

Deductibles play a huge role in insurance.

We recommend creating a Role Scorecard which is a hiring strategy from the book Who: The A Method of Hiring.

I would try to not let emotion play a role here and outweigh what it says on paper as to what makes the most sense to do- ergo being too eager to have one buy and hold property if it made more sense to sell. 

That team should consist of three roles: an agent, a general contractor, and a property management company.

Take a personality test like the DISC profile to get a better understanding of the role you might play in a real estate team or partnership or venture.Now, you can find a mentor that best aligns with all the above.

I think I would ask my self what role are these properties going to play in my retirement.