Holland's role would probably be a special advisor, but I recall hearing that he might have similar offers from other organizations, including Detroit.
Regarding the next GM, I'm pasting my thoughts from the other thread here-
I'm starting to wonder how big the role of the new GM will actually be, since the Oilers have made some significant long term decisions the last few years. Knoblauch got a three year deal, and Jackson also hired a director of analytics and a new scouting director. Now Seravalli has been talking about "the organization" already working on deals for Janmark and Draisaitl. That begs the question of who exactly is doing all of this?
I'm feeling more and more like Jackson will be involved in all big decisions, and the new GM is isn't going to be in charge the way Holland or Chiarelli were previously. Jackson is far more involved than Nicholson was. This setup feels more like Calgary under Treiliving and Burke, or Toronto with Shanahan/Dubas. The GM will do the day to day work and have some transactional autonomy, but bigger picture issues and organizational hires will ultimately be Jackson's call.
That probably impacts who we will be able to hire. A lot of GM candidates want total autonomy over their hockey ops department. Coming into a team where you can't pick your coaching staff, scouting director, assistant GMs, etc, is a different animal. I wonder if either Brad Holland or Gretzky get a bump into the GM's chair this week. The other option would be someone that Jackson has a strong personal relationship with, and who he may have been quietly engaging with for a while now (e.g. Dave Gagner).