personally, I'd be happier if, say, after you beat the Elite Four 50 times, his Pokemon's levels all go up by ten
with Red, that would put his Pikachu and level 98
this is what his team should be
Pikachu: level 98
Espeon: level 96
Snorlax/Lapras (should change on day or time battled?) level 96
Blastoise, Charizard and Venusaur: all level 97
something hard, yet challenging
or, god forbid, a double battle with Red and Steven