As an Ash fan I'm torn. On one hand I want Ash to win to drink the tears of Cynthiafags. On the other hand I want him to lose because if he wins he'd have to face Leon and that would be disastrous for the narrative going fowards into Gen 9

>If Ash beats Leon then he's #1 in the world and there's really no where for the series to go after that without some absurd power creep
>If Ash loses to Leon then he would be WAY too close to the finish line for him to start over with a new team rather than just keep training with the current one

Since he beat Iris and Steven he's already solidified his place as a true Champion-level trainer. But if he loses to Cynthia it would leave it nice and ambiguous where he stands in regards to the rest of the Champions and also establish that he still needs to grow some more before he's ready to try again which would lead nicely into the next fresh start in Gen 9.
On the other hand the undeserving smugness coming circlejerking Cynthiafags for months following Ash's loss would be totally insufferable.

And no you dumb faggots Ash isn't going to be retired after Journeys. He's way to reliably bankable for TPCi to ever even consider letting him go.