[CaptainYooh]

Originally Posted by Enoch Root

I think you've missed one. The way I see it:

1.0 was the Gagner, Cogliano, Brule, Schremp era, circa 2007-09
2.0 was the Hall, Eberle, Paajarvi, Omark, Hemsky, Penner era, circa 2010-12
3.0 was the Hall, RNH, Eberle, Yakupov, Schultz dynasty circa 2012-14
4.0 was the McDavid, Hall, Draisaitl, RNH, Klefbom era, circa 1015-19

1.0... "Honestly, I see 600 goals and 1,300 points!"
2.0... Oil Change - here come the Oilers!
3.0... Three #1 overalls - "it isn't a question of if, but how many!"
4.0... McGenerational! "It's a big change in Alberta, and it won't be changing back soon!"

...

That's a pretty good summary. However, it should be illustrated by respective GM's assessments and promises accompanying each rebuild.

Like this one from 2010:

Lowe said the Oilers had a new plan for success, to a certain degree modeled after the Chicago Blackhawks’ ability to build around draft picks Jonathan Toews and Patrick Kane. He also plans to hire a general manager based out of Oklahoma City — the franchise’s top minor-league affiliate — who would be in charge of scouting out players other franchises might have missed.
"We’ve got to draft and develop here, more focus on resources spent toward development that will ultimately filter up to our team in Edmonton," Lowe said. "To me, that’s the formula of success. So, that bodes well for Oklahoma City here. We’re definitely going to focus on spending more money on the development side of things."

2013:

"Let me be clear: the Edmonton Oilers are not where they should be right now and that is unacceptable and we need to get better immediately," said Kevin Lowe, the Oilers' president of hockey operations. "That starts today with the announcement of Craig MacTavish as general manager and Scott Howson as senior vice-president."

2015:

Sounds like the makings of Rebuild 3.0, but MacTavish says that’s not at all what he’s thinking...
“Right now we’re not good enough and we’re not strong enough or deep enough, but we’re closing in on that,” he said. “As we see this team going into the future, I see the potential of another great Oiler decade.

February, 2018 (before the trade deadline):

“This isn’t really a postmortem,” Chiarelli said of fans having to wait for the Oilers, currently sitting tied for 26th and 27th with the Montreal Canadiens in the 31-team league with 22 games remaining in their season.
“This season has been a tough one and we’ll get into that at the end of the year. I’m not trying to avoid the question because there are some obvious questions.”

All subjectivity aside, in the past 20 years, Edmonton Oilers have been no good for all but one season in 2005-2006, when they had Pronger and, coincidentally, great goal-tending out of Roloson. That is all. One good season.