Best guess at how many more years Sid plays before retiring? Is passing Jagr for #2 all time and/or 2000 points important milestones for him personally if you had to guess?
I don't think those numbers are terribly important to him. I'm sure he'd love to reach them, but I don't think it's what drives him.
How much longer he decides to play depends on many variables:
How is his health? (Avoiding concussions is very important to him)
What is his level of play?
Are the Penguins showing signs of improvement?
To me, those will be the big questions next summer, when only one year will be remaining on his deal.
I could see him retiring after the 2026-27 season if any of the above three questions don't have the desired answer.
But because we're having fun here, if I had to guess, I'll predict that Crosby's final NHL season will be the 2028-29 campaign. Just a guess, though. If he goes out by winning the Cup 20 years after his first one, well, wouldn't that be just about right?