I voted option #3. I think the wording may be a bit strong though, but still.
Crosby in my opinion is #5 all-time after the tier of Gretzky/Lemieux/Orr/Howe. Maybe some have him a few slots back than #5, but I think he has a solid case for #5.
One player whose often brought up as "the best player to never win a cup" is Marcel Dionne. When history forum ranked the top 100 player of all-time in 2018, Dionne slotted at #63. Again, you can have him a few ranks higher/lower, but #63 is a reference point.
That's a hell of a high bar to go all the way up to #5 without a cup, when the previous best player ever without a cup is #63.
I get that a cup is a team award and one player alone can't win - but still. I think it will definitely hurt his legacy if he doesn't win at least one cup.
Does McDavid put up many more playoff runs like the one in 2022, and does the narrative become "wow, one of the absolute best playoff performers ever, too bad his teams let him down and he could never win a cup!"? If that happens I suppose that yes he could pass Crosby all-time - but I do think it would be hard.
For what it's worth - I'm very confident McDavid wins at least 1 cup.