That's exactly what I did when I was in your situation...I would 100% do it again...Things I did well-Found one that was a for sale by owner that needed some work - gave me a lot of rehab experience-Fixed rental side first then lived in and worked on my side-Use Postlets and Craiglist plus yard sign to advertise vacancy-Change my voicemail message to explain all details of property = saved me many calls explaining the same thing.Things I would do differently-Read the tenant screening book on this site first -Always do open houses instead of individual appointments-Ask people to bring their dogs if you allow to appointments-The location of house was great for all things in my life; but would consider moving sooner to have multiple duplexes with owner occupied financing

You have a screen your notes, borrowers, etc. 3. 

Do you just want someone who is handy that can fix some of the problems that will arise or are you looking for someone who will list the property, screen the tenants, etc.  

Aside the usual due diligence/screening and placement of tenants, payment of property taxes etc, what are other items I need to point out to him during our meeting?

He had no tenant screening process no background checks and so on. 

PM or no PM, screening tenants is critical.

Also screening tenats in a duplex can have issues have you experienced those in the oakland home or has it been all good?

In a rent to own, you make payments through he home 'asset' (TV, Washer / Dryer etc) being paid off. 

In this case its 3, 4, 5 days per week, or another way to look at it he is there at least half the time.My issue is first he is not screened, he has a key, he is using water which I pay for, and his car occasionally causes parking space congestion.I am going to have a talk with my tenant about this, but there is nothing in the lease that prohibits this.  

I can recommend using mysmartmove as part of the screening process.