I just don't think everything Tiger needs to line up perfectly will line up perfectly for him to reach Jack's record. Gotta be healthy. Has to be playing his best golf. Needs everyone else to be playing so-so golf. It helps to be competing on major venues where he's had success. Needs decent weather where the wind isn't an issue.
Augusta... it'll always be his best chance, but Jordan Spieth was 12-yrs-old the last time Tiger donned a green jacket. US Open: Pebble Beach in 2019, Torrey Pines in 2021. Beyond that, venues aren't lining up the way they need to. PGA: Bethpage Black in 2019.
Open Championship: St. Andrews in 2020.
But of all these things, including his health, it's no longer just about how well he plays. It's also how well everyone else is playing. It used to be assumed that if Tiger was playing well, it wasn't if he would win but by how many strokes he would win. It was a given. Those days are gone now, the younger players are light years ahead of the younger players back in the early-mid 2000's. They have to adjust to a different life, sure... but it doesn't take 5-7 years for these young fellas to win these days like it used to.
Considering that he hasn't hoisted a major trophy for going on 9 years now, that he's not the same player he was back in his prime, that the tour is a lot more competitive than it was when he last won... he's needing a lot of things to line up in his favor, several of which he has absolutely no control over.