The problem when you look at Hill or Kuemper (Bob was plauying absolute elite hockey and has proven he can be an elite goaltender in the past) is that both Vegas had completely stacked teams that just don't happen often. Vegas has one of if not one of the deepest D cores when they won as. well as perhaps one of the deepest forward groups in a long time. Colorado also had an incredibly deep D-core and won with a 3 future hall-of-famers. There are always going to be exceptions like that, but if you look in the past, outside of St Louis you either need a stacked team or an elite goaltender. Dahlin, while nice, isn't going to suddenly make our defense elite. Lacking forwards isn't going to suddenly make us a deep contender and when we finally have that he'll be in his late 20s and we still don't know if we'll have anything close to competent goaltending. I don't want to be Edmonton or Toronto, constantly let down by lack of stability in the crease.
An elite goaltender (if asky can become that), is the equivalent of a franchise QB in football. You can win with that almost singlehandedly, but if you don't have that you better have a historically good team around him (like Baltimore did with their Defense and Trent Dilfer as QB or TB with Brad Johnson).
I really disagree with "Dahlin, while nice"... there are only 6-7 D in the league who can claim to have Dahlin levels of impact on each game. IF! If Askarov becomes a top 5 goalie who doesn't have massive ups and downs, then he can claim to be that impactful. He hasn't proven that yet.
The franchise QB of the hockey team is either a true #1D like Dahlin or a true #1C like Celebrini. But there's no single player on the ice that makes nearly as much impact as a franchise QB, so it's a bad analogy. Franchise QB is the single most impactful position in team sports, nothing else comes close.
Goalies of dynasties or cup winners in the cap era:
PIT - had good goaltending with flower, albeit very inconsistent
CHI - never had great goaltending (so, same as COL, VGK -- starting to look like an archetype, not one-offs).
STL - while Binnington played well, it was the depth and size of the lineup that beat teams down to win their cup (similar to VGK but less flash - some same players tho!)
and on the other side of the ledger - good Bob, Vaselevskiy, good Quick, one-off from ANA with great goalkeeping.
So, not at all clear to me that Bob, Vaselivskiy, and Quick are requirements while you have just as many counterexample dynasties without a clear franchise goalie, plus on the other side, the franchise goalies who haven't even sniffed it, like Shesterkin, Hellebuyck, and many before them. Meanwhile pretty much every cup winning team has a D man who is playing like a #1 (Blues/VGK had Pietrangelo and the others are self evident).