I personally think that this is a great idea. Anyone who really knows their stuff about pokemon will flock to the opportunity to show it off. The only thing I'm concerned about is whether or not we could show the thought process behind the moves accurately. After all, everone's different, so I might respond to a particular situatuion differently to everyone else.
We could also make it clear that, say, Bob is afraid of scarf heatran because his team also has CB heracross and DD Salamence, whereas Jim isn't afraid nearly as much, because he's got a bulky Milotic and a Scarf Flygon.