Off the top of my head, my suspicion was that not many recent cup winning teams had their starting goalies win all 16 playoff games. Turns out I was wrong, but I also looked at whether they were the defacto #1 for that whole season or not (lower GP might also have been due to injury)
Playoff wins by starting goalies in cup winning seasons: (reg season GS that year)
Holtby: 16 (54)
Murray: 7 in 2017 (47), 15 in 2016 (13)
Crawford: 13 in 2015 (57), 16 in 2013 (28)
Quick: 16 & 16 (68, 49 in '15 - injury?)
Thomas: 16 (55)
Niemi: 16 (35)
Fleury: 16 in 2009 [and 9 in 2017] (61 - 2008 + 34 & 46 in '17 and '18)
Osgood: 14 (40)
Giguere: 13 (56 GP - no GS stat on hockey ref before this year)
Ward: 15 (28 GP)
Khabibulin: 16 (55 GP)
Looking at the times 'elite workhorse ' goalies got to the finals, their GS was lower than typical:
in '12 when Brodeur started only 59 that year (he was 39 yo...)
Lundqvist started 62 in '14
Luongo 60 in '11.
Rask (34 - lockout year), Bishop (60), Jones (65), Rinne (59), Fleury (46).
Conclusion: Riding one goalie for 60+ starts in a season is unlikely to end with him raising the cup over his head. Even if you have a bonafide #1, their best playoff runs come when their reg season GS were kept under control. You rarely need your backup to win more than 1-2 playoff games, but you want them to take at least 25 reg season starts.
Rittich has started 25/49 so far. As painful as it was to see Smith get the nod so often, it's been hugely important to keep the end season number low. Riding him too hard early would have been a recipe for disaster.
I think Rittich has every potential to join the list(s) above. I also think you want to go into every season with two goalies who you wouldn't be unhappy to have start 50 games. Ideally this can be achieved for under $7M total.
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