Also remember that nearly each time Conway was defeated he would lose by a move improvised by his opponent like Gible biting Shadow Punch, Grimer using Poison Gas to deflect its own Sludge attack that was deflected by Venonat's Psychic during his practice match with Dawn at the Camping mini-arc. Like Max, he knows stuff by the book and the fundamentals of battle to come up with unique strategies.
Now the reason for me digging up DP information is to support my case with Trip; he is similar to both Max and Conway in that he has advanced strategies for a rookie trainer. Remember in episode 10 when he literally raped Ash's team of 5 Pokemon at the time? Tranquill and Frillish had amazing strategies put into place and he uses his Pokemon's abilities to his advantage like Paul did in his battles.
Though he has those strategies in place, he has lost based on the fact that his opponents come up with tactics that are improvised like Bianca who I think is the best example. By stealing the pillars to take out Conkeldurr (I think Emboar used a cheap variation of Thief but it can't learn the move so I'll just move on...) was something I'm sure that Trip never expected and cost him the match.
To me I think those losses further effected his notions about power because even though he never admitted it when drawing with Ash in their third battle or losing to Bianca he probably thought about how even with the best strategies there is always room for an upset. Just look at the way he had Bianca on the ropes, blocking her attacks foiling her all or nothing style of battle in an attempt to overwhelm his opponent. Then going on the offensive literally keeping Emboar from doing anything and it being tired left it wide open to be finished off with Stone Edge, but then the battle turning against him had to effect him in someway.
So, I probably expect something to happen like this in his battle with Alder.
And "As a true champion, however, Alder takes everything Trip dishes out."; guess this means that he will take the match seriously and it makes sense that his Pokemon would be able to take even the strongest moves that Trip can deliver. Wonder if Buffron's Afro will be used to lower the damage from attacks like against Pikachu...
Kind of reminds me of how Cynthia's Garchomp used its fins to block attacks, but either way I can't wait to see what happens in the end.
One more thought; its cool that Trip studied up on Buffron, but what if Alder decided to use another Pokemon instead?? Oh well, looks like he got lucky considering that is the only Pokemon that he has ever seen him using before for that matter.