Interesting post, and agree overall with the gist. Just curious on your take why would he fail at United?
It's basically because people think that he would suddenly be brilliant if he was given:
a) Money
b) Better players
The reality, thus far, though has been:
a) I'd struggle to think of a signing he's made that's improved Spurs that was a big signing. It's always been the case at Spurs that we've done well out of cheap signings than big ones. His history at Espanyol, Southampton and Spurs is littered with expensive failures, and as a Spurs fan you hear rumours from "ITK" about the ones we get offered and he didn't want, like Tielemans.
I just don't think he has an eye for a player.
b) The height of his powers have come when managing players of a lower reputation - look how he's handled unhappy "stars" at Spurs - Walker, Trippier, Alderweireld, Vertonghen, Eriksen, Adebayor, Kaboul and so on. His solution is worse than the way people complain about Mourinho. He'd do no differently to OGS imo - cast out the "stars" and rely on the lesser players.
In addition to all this, a lot of the complains about Pochettino's time at Spurs have been about how "Levy doesn't back him". By observation, Woodward is certainly no different, potentially worse, and so he'd hardly find himself able to get a Dybala at the drop of the hat. United were linked to the same players as spurs for most of the off-season (NDombele, Fernandes, Dybala etc.) and got none of them, so I'd be wondering about that.
The bigger issue though, which Mourinho will inversely benefit from, is that he's not going to get a hug and a blowie from the United board for "having a go" or reaching a final - they will want him to win. This is a problem, because he's so far been a serial bridesmaid at Spurs - unable to cross that final threshold.
The last, unknown issue, is the Harry Kane factor - how much of Kane was due to Poch, and/or how much of Poch was due to Kane. Just like Bale dug out AVB multiple times (which the lesser observant of Spurs will see), a good majority of Spurs' results in the last 12 months have been tumescent football rescued by Kane's clinicalness. Even throughout the 'better' first half of last season, we played terribly but managed to grind out results somehow - it was never that convincing, but we'd all assumed it was one of the Fergie things about how a good team still wins points when they play badly; it just turned out we'd play badly all season (including in the CL) and look good in spite of it. I don't think we had a single CL game where we looked convincing (especially in the final), but we managed to prevail by a series of miracles.