Yes and no, he could have definitely played at a higher level but the only serious club that have been in for him in the last few years are Arsenal and they decided they’d rather pay £70m for Nicholas Pepe. Levy didn’t want to pay more than £15m for him which was never going to fly and Everton was never a serious option. Assuming he gets a good move this summer and experiences European football for a few seasons I don’t think he’ll look back on his career with loads of regret, he will go down as the GOAT of the club he grew up in the shadow of whilst hopefully winning something by the time he hangs up his boots as well. Also been paid a top wage in the meantime.
As for Olise, these are different times and the club’s model will be to sell these young talents, not hold on to them. Back when Wilf was entering his prime we just didn’t have a choice due to a lack of resources and the club not being particularly attractive to good players.
Also, we only paid £8m for Olise due to a release clause anyway so stands to reason that his agent won’t let that happen.