I was going to post more about this next round, but it's reinforcing your point here so I'll add it now. I dropped Dryden out of my top 8 this time, and one of the big reasons is that I feel strongly that his team bailed him out a lot more than the other way around.
I made a similar observation to you when looking through the game logs, noting how frequently it seemed that the other team would score not just the first goal, but often the first two goals, but then the Habs would come roaring back and win 6-3 or something like that anyway.
I counted up the games where Dryden's opponent had what I'll call a "winning position", which I'll define as leading by 2 goals at any point in the game, or leading by 1 goal at any point in the third period.
Winning positions against Dryden's Habs:
Boston 1971: 4 of 7 games
Minnesota 1971: 2 of 6 games
Chicago 1971: 5 of 7 games
NY Rangers 1972: 4 of 6 games
Buffalo 1973: 3 of 6 games
Philadelphia 1973: 3 of 5 games
Chicago 1973: 4 of 6 games
Vancouver 1975: 2 of 5 games
Buffalo 1975: 4 of 6 games
Chicago 1976: 0 of 4 games
NY Islanders 1976: 3 of 5 games
Philadelphia 1976: 1 of 4 games
St. Louis 1977: 0 of 4 games
NY Islanders 1977: 2 of 6 games
Boston 1977: 0 of 4 games
Detroit 1978: 2 of 5 games
Toronto 1978: 0 of 4 games
Boston 1978: 2 of 6 games
Toronto 1979: 1 of 4 games
Boston 1979: 6 of 7 games
NY Rangers 1979: 3 of 5 games
It's honestly wild how much the 1971, 1973, 1975 and 1979 Canadiens repeatedly bailed out Ken Dryden from what would ordinarily be considered losing positions. They were trailing by 2 and/or losing in the third period in 37 out of 64 games in those 4 postseasons, 58% of the time, and yet still miraculously turned that into 3 Stanley Cups.
At least there is the 1976-78 stretch which is what a dynasty should look like, consistently closing teams out without much trouble. Over those 3 years the Habs were in a losing position in only 10 of 42 games (24%), and the Islanders were really the only team that gave them too much trouble. For reference, Plante's Habs during their 5 Cups in a row faced a losing position in (edit) 13 of 48 games (27% of the time).
Then there's also this:
Winning positions against the Habs without Dryden:
NY Rangers 1974: 3 of 6 games
Hartford 1980: 0 of 3 games
Minnesota 1980: 4 of 7 games
Those don't really look that different than most of the Dryden years but for whatever reason the team didn't score their way out of trouble. In short, I'm a lot less convinced by the "they won with him and not without him" argument than I was previously.