>>53269730I think you're overestimating the pull Pokeshipping has on its own.
Yes, a massive generation might find it gratifying, but I don't think they'd care AS much unless they timeskip or something.
Most Pokeshippers were Pokeshippers when they were the same age as the characters themselves, now many of them are three times as old as Ash and Misty and probably find them less relatable as a result.
If they REALLY wanted THAT demographic we'd see Ash's dad by now. Ash would start aging as soon as MPM started kicking in and each episode would be a series of vingettes set at different times
All of which is too big a leap for pokemon