Jud:
Somewhere in the vast archives of GCA, there's a thread that I started in which I suggested that Tiger had to go low to win majors -- of his 14 majors, he's been -11 or better in all but three of them. Admittedly, a few of those (notably Valhalla PGA in '00) lots of folks went low, and one of those (Pebble Beach) Tiger went crazy (he was -12; the best the field could do that year was +3). Jack was -10 or better in only two of his majors.
Again, lots of caveats because of course set-up and conditions, but I'm of the view that tougher course set-ups do not benefit Tiger in majors. Instead, they seem to let more people compete with him on relatively even terms (which was the opposite of what Jack felt; he loved hard conditions in majors, figuring few had the nerve and patience to stay with him for four rounds in harsh conditions and tough set-ups). Everyone points to the PGA at Hazeltine, when Yang outdueled Tiger down the stretch, as the Rosetta Stone of Tiger's vulnerability in majors. But I've always thought it came first at Augusta in '07, when in brutally tough conditions (the course had been lengthened, rough grown in, trees tightened things, and the weather was cold and windy) Tiger lost a lead in the final round to a young gun (Zach Johnson). And he lost not just because Johnson played well, but because of things -- course management, short game saves, putting -- that continue to plague him today in majors. Johnson beating Woods then was far more surprising to me than Yang beating Woods -- because the conditions seemed perfect for Tiger to grind out a win. Instead, he faltered. That to me was the first real crack in his armor in his pursuit of Jack's record.
I'm also (partly) a horses-for-courses theorist, and Tiger lost a big opportunity in 2010 to win majors at two courses (Pebble, TOC) where he'd won before. He struggled at Congressional in '97, came close at Sandwich but didn't win last time around, and was a non-factor in '01 at Atlanta.