The first hurdle I am trying to take is identifying a 2-3 good markets to invest in.

I agree, but like you said, I need to be able to identify an area before there's a need for an agent.

What's the best way to identify section 8 owners?

I bought a list from ListSource, but it was difficult to identify the criteria for Commercial Multi-Family. 

With such a distance, having a team that acts quickly, has open communication, and identifies market trends, i.e. suggests rent increases based on the market, are all huge pluses in my book.

I would suggest the following:1) If possible, identify specific properties you are interested in2) Find out the owner from public records3) Sent them a letter describing your interest and asking for 10 minutes of their time in person or on the phone4) Network with others in the area to see if you can find someone to make an introductionHope this helps,

Helping you to understand the flexibility and limitations that come with using a self-directed retirement plan to invest in real estate is the bigger issue, and will vary considerably based on what kinds of investments you look to engage in.There are a lot of good threads here in the BP forums on the topic, and you will be able to pretty quickly identify those plan providers who take the time to thoughtfully contribute to the community. 

Where I have the tendency to take a built for speed, big vision-casting, build the plane as we fly approach, and am highly energetic and relational, she is able to identify contingencies, execute details, and can easily be stern/disciplined with people as needed.

Which then means I need to figure out what metro to invest in and start building a team there so I can be ready to jump in a couple of months when the house is sold.As to what I enjoy, I really like identifying properties and doing deal analysis and making creative offers to get deals done. 

The original plan was to acquire the property via a land contract to rehab and sell for retail but was able to identify a buyer at $60,000 within 7 days.