Well we're at year 10 now and I don't think this team is good enough to win the Cup... again. Emberson and Podz are okay, but they're not as good as the guys they replaced who the Oilers basically lost for nothing. In fact most of the Jackson/Bowman acquisitions in the offseason have been middling at best. Even the much vaunted Savoie as pointed out earlier has not had the greatest returns so far.
As for Ken Holland, I rag on him for inept drafting (zero draft picks currently playing for the Oilers) and several bloated contracts/bad acquisitions (Campbell, Nurse, AA, James Neal, Zack Kassian), which outweighs the good he did (Ekholm, Hyman, Knoblauch). The team did almost win the Cup, you're right. But in the game of life, almost doesn't count for anything.
One of my biggest gripes with the Oilers over the past decade plus is that they've always had reactive management, never proactive. Waiting until the problem becomes so big it cannot be ignored is not a viable solution in sports. I could care less if Bowman's only been on the job for 4 months. Your job starts when you're hired. And through a quarter of the season the Oilers aren't even in a playoff spot staring up at the team they're likely going to have go through if they want to have any chance of winning the Cup in Vegas. If he's "not pleased" with the team so far then do something about it.
"At one point" was like 6 years ago. His stats since the Ducks took a tumble are atrociously bad.