An actual intelligent perspective on this, yesterday, by the fine Bruce McCurdy (Oilers' expert since the early 1970s):
Connor McDavid turns 28 today, and his Edmonton Oilers are aging right along with him
My take would be that Peter Chiarelli did a lot of harm. He made about two good moves and ten or eleven terrible ones (Griffin Reinhart... trading Ryan Strome for 25 games of Ryan Spooner... getting only 1 stay-at-home Dman for future Hart-winner Taylor Hall... out-of-nowhere 4-year overpayment for Mikko Koskinen... etc.).
Because of Chiarelli's incompetence, the very promising 2016-17 season (the Oilers' best in almost 30 years) went for naught, as the 2017-18 and 2018-19 seasons were total wastes and could be added to the "decade of darkness" to make what I refer to as the "thirteen years of thirst".
But starting in the Holland-era, from 2019-20, the Oilers have been competitive every season and made the playoffs five years in a row, almost surely to be six this year. They won the division in 2022 and won the Conference (quite an achievement nowadays) in 2024. One win away from the Cup.
Holland made his share of bad moves, too, but not overly many and at least you could see what he was prioritizing --- basically dependable veterans, and trying to build up the depth in case of a Cup run.
Nobody really saw the Bowman-hiring coming, but here we are. The interim period with Jeff Jackson seemed to leave the Oilers' vulnerable for a few weeks, as St. Louis swept in with an offer-sheet to take two promising younger players away. Kind of a crappy job there.
So, has the organization done enough? If the Olers win the Cup, then yes. If they don't, then... I dunno. It's on the fence, maybe depending on how they make out this season and next season.
(We pause here to note that drafting superstar players in the Cap-era doesn't mean you're logically a favorite to win a championship. More so, it means that you now have to pay a lot for those superstars and then have less remaining to pay the rest of the depth guys needed to win.)