I just want to say I don't think the rebuild started in 2006 it was a few years after 2009 or 2010 I'd say is when it started. It's a minor detail but I wanted to point it out.
How will history look at the era now? It's hard to say it depends on how the story ends. If the Oilers become a Stanley Cup Champion then it'll probably be looked at as a success. I think as stated earlier if they do become Stanley Cup Champions it'll probably be looked at as a change of the guard of the 80s era management to this new group. I think if the Oilers become a consistent playoff team it will be seen as a positive but probably a bit disappointing with all these #1 draft picks not paying off in the long run. We'll just have to wait and see what happens.
I used to have a hard line of that, to point out that it was 2010 or 2009 at the earliest, but I do understand that 2007-9 was a rebuild of sorts. The whole concept of picking a date only started with Sutter in Calgary anyway. He made a public spectacle of saying that he had a five year plan, which I'm pretty sure no one did before, and he even said that getting Kiprusoff sped up that deadline. Not surprisingly, he was fired when the team started doing badly in year 5 of his declaration, and imo that Phaneuf trade was done because he was in year 5, and not for hockey reasons.
That deadline aspect of it is dangerous imo. I don't want management to think that a move MUST be made because of an arbitrary deadline. Just because a trade is huge doesn't mean it is the right move for that time and will spark greatness. However it's been year 5 since drafting Hall and maybe that mark was what sparked Katz to get Nicholson and for Nicholson make the changes he did.
In terms of how this will all be remembered, sports are fickle arenas. If we start winning, history will be on our side. There will be a grumpy minority that will be ho-hum about it, but that group will be chiseled down because it's not a fun group to be a part of. Also, as bad as the rebuild has seemed at the time, it has only been 5 years of torture. That is a lot but won't seem that bad in retrospect.
I would argue that what we suffered was better than the torture of what teams like the Isles, Canes, and Panthers have suffered through, hanging around just outside the absolute bottom for many years. The lesson around the league might be that if you suck, you might as well suck as bad as the Oilers did. At least that way you are missing the playoffs but getting top talent. Management can change, and after a quick purge those top players will still be there.