What is there to gain and what is there to lose?

Charlie and I had a great lesson with John yesterday.  He was working on cross country, so after warming up, we met him out there.  I told him I've been having problems with show jumping; I just can't get Charlie to lift his legs up, even when we go clear, but I figured John would diagnose it and could look at us jumping cross country just as well to figure out what the problem was.
We started with a little log, and then proceeded to jump our way around the course, doing some new stuff that was really fun.  And thankfully, far off in the distance until I was right up on it so I couldn't get intimidated.  We jumped a chevron, a three log split rail, a table with some cut outs, then a roll top to the up bank down bank skinny, down the long aisle to a bigger table with cut outs, into the woods for an angled fence, and around the corner to a roll top, ditch, skinny, then down the long side over the ditch with the wall behind it (!!), and then into show jumping where we did an oxer, right hand turn, vertical six strides to oxer, left hand turn, vertical with 1 stride to another vertical (that looked like a whopper) with five strides to another oxer.
Charlie jumped everything like an absolute champ.
John said he was surprised we hadn't signed up for Training at Caber and I said I had wanted to but got talked out of it.  He asked me to think about what there was to gain and what there was to lose, and if the potential gain outweighed the potential loss, I should go for it. 
I went home and looked through everything - the dressage test (I rode it today to try it out), champs, any year end awards, and my schedule, plus the things that can't be weighed because they're too uncertain - my goal to go Training, and the thought that who knows what can happen over the winter, and then asked to change my entry to Training, withdrew from Aspen at Novice, and signed up for two of the three derbies at Training.
So here we go ...
Riding Charlie over those wide tables was AMAZING.  We were actually in the air long enough to feel the difference, and Charlie just went for it with such gusto, like he really loves his job.
John's take on the pukey show jumping is that Charlie's strength - going fast - isn't utilized in show jumping, and then to compound it, I get nervous and try to suck him back, which just takes away all of the impulsion and he has to puke over each fence.  When John made the fences higher and harder so I couldn't spend as much time screwing around and just had to concentrate on riding and getting over them, things just flowed. 
Charlie isn't challenged by novice, and then I suddenly remembered our first lesson at John's, where he was talking to Shannon about how much better Charlie was when he went Training than Novice, because at Training he actually tried.