Just some ideas:
I thought about having a vote to see who would make the initial group of inductees and then I thought, isn't that being a bit presumptuous. This is Celticsblog and it is someone's baby, so to speak. So besides inducting Jeff I think it should be Jeff who decides who are the first group or two or three groups to be inducted. After his choice of inductees the initial time maybe the inductees decide together who to nominate and Jeff decides who is inducted.
My reasoning here is that the guy at the top, Jeff, knows better than anyone else who has been most important to this site and who deserves such honor. Heck, there could be someone behind the scenes who none of us have ever heard of who could be instrumental in Celticsblog being what it is today that needs recognition. Jeff, more than anyone knows who these people deserving such credit are. Also, there could be people involved at earlier stages of Celticsblog that are no longer a part of this community that few here remember of know about. Jeff would know who those people are.
Also, I'm not a huge fan of turning this into some sort of popularity contest. It should be filled with contributors who Jeff and maybe later on others truly helped to shape, preserve, and nuture CB into what it is.
I don't think I can stress this enough. I think it would be a huge mistake to put the nominating and voting of members into the hands of the membership.
Something that might be interactive for the membership could be the nominating of posts, threads, articles, and interviews and then possibly the voting on the most deserving of those pieces. There could be an area where there would now be posts of the year, thread of the year, article of the year and interview of the year. A thread could remain open all year for people to nominate these pieces. The Hall membership could narrow it down to three and then membership could vote.
Then, each year, just as everyone is returning to CB for opening game, Celticsblog could reveal its newest inductees and the results could be announced for the yearly awards.
Anyway, just a few ideas.