Questions to ask local experienced investor

[Eric F.]

Long story short. A successful local investor (buy and hold, also a broker for 30 years, runs a small real estate investment company now) taught a creative real estate class here in Raleigh recently and offered anyone a chance to meet with him for an hour and pick his brain. I am of course taking him up on it, this Wednesday. He said to bring a rough idea of what I want to do and some questions.

My goals are to accumulate buy and hold properties to generate passive income, enough to live off in 10 years if I desire. At first I plan on being very hands on, but in the long run I'd like to move to more passive with property management so I can travel and volunteer my time. In addition, I am interested in other types of real estate investing, mainly rehabbing. My plan starts with buying a 2-4 multifamily using a FHA loan and owner occupying, and from there I hope to slowly build up a portfolio using traditional and creative ways, like subject 2, if possible.

Questions include:
*What areas of town should I look into?
*If you were starting today, with my end in mind, what would you do, who would you meet with, and so forth?
*How realistic does my plan seem?
*If real estate starts working out, should I look into becoming a broker (and yes I know this is discussed in 4,000 BP threads haha)
*One of my plans is to send yellow letters to a bunch of absentee owned multi families in town, I plan on asking his advice on this.
*Where do you see Raleigh's market going?

and the most important one (in my opinion): Is there anything I can do to help you or someone else in exchange for knowledge and instruction?

Am I missing anything super obvious? I only have an hour and do not want to waste his time.

Thanks everyone!