Cup campaigns will probably make or break this season in particular, and his future here in general.
In terms of league, I don't see us getting out of the purgatory that we're in at the moment. Our matches are virtual coin filps due to end-to-end, high variance football Ange gets us playing. So, I expect us to go on a run at some point. Like how you'll find instances of runs in consecutive coin flips. That'll make sure we won't get stuck in the bottom half. However, at the same time, a way larger sample since last November tells us that we're a mid-table team. So we'll probably neither sink nor swim, but float somewhere between 4th and 10th.
That being said, cups are an entirely different story due to their one game shoot out nature. If what I said about our matches being coin flips is true, then it's certainly conceivable to go on a run and win at least one of them. There being three of them only increases the odds in our favour. So if Levy-board already have no reservations about him despite 13 months of mid-table form, then a cup win would certainly win them over to give him at least another season. Unlike this summer, they may even consider going all-in in the market according to his wishes.
So make of that what you will. If you think we're a cursed club then go assume that we'll go to the final of all 3 cups only to lose each of them in penalties. If you tend to live in the clouds then assume that he's a lock for winning 3 trophies this season. Both are within the realms of possibility.