I don't think a decade or two ago Ole would have been up there with the top coaches - I suspect he would have been a mid table coach who gets a go at Spurs at some point. In this era though we've actually got a lot of coaches around Europe who haven't won much. Good managers but sometimes struggle to get over the line.
Even Klopp was like that for a long time - always getting to finals and losing. Or Pep has a weird mental block about the CL these days it seems. But they are nonetheless winners, while there are guys like Poch and Rodgers who've hardly won anything but are still regarded as top coaches (albeit well done to Rodgers on the FA Cup win, could be a platform to build on). Weirdly Tuchel is the opposite - doesn't get his teams playing nice stuff but seems to know how to win.
You'd have to say Simeone, Klopp, Pep, Conte, Flick and (perhaps) Tuchel are genuine world class managers and there aren't too many others. So yeah I think Ole deserves some respect, despite probably not being at Man Utd if we were in a different era where there were more top managers around. In this era he's up there, and until a world class coach is available why would we gamble on some other nearly man rather than backing our own guy.