Tiger's competition is deeper -- the courses have been made considerably harder in most instances since Jack's time and while the equipment is on Tiger's side -- I believe he would do as well, if not better, than if their were a rollback in equipment whether the club, ball or both.
Matt, just a couple considerations here.
Deeper competition doesn't mean better, necessarily. Between them, Palmer, Player, Trevino, and Watson have 30 majors and about 120 other PGA wins. There's considerable overlap with Billy Casper as well, and he's another 50-event winner, plus Gene Littler's 29 wins and Ray Floyd's 22 and 4.
By comparison, Singh, Mickelson, Els, and Stewart have 3 each for 12 total majors.
So the older generation had more events, and therefore more chances to win. But that's more weeks you have to psych yourself up for the event. and they didn't have the luxury of (say) blowing off Kapalua or any event past Labor Day.
Also, and I am not old enough to really appreciate this, but so many 3-footers I see in vintage footage look like a stab and hope, as opposed to today's near-formality. Surely that disadvantaged the better player 40 years ago, as opposed to the tougher courses you mention, which would benefit the better player.
Obviously comparisons are tough.
I'm still in the "Tiger will pass him sooner rather than later, but not quite yet" camp.
(Edit: removed reference to Jack's schedule.)
(2nd Edit: Tom, just saw your note. Yep, I realized that didn't sound right, so I double-checked golfstats and you're right.)