wow, thatnks everybody for the input and please keep it coming. I have a couple followup questions then. It seems almost unanimous that everybody hates the 75 foot rope and says to go to a max line length of -15. Why is that? What is so different from 60 to 75 feet. With the verdict being nearly unanimous, I'll probably go that direction regardless of reason, but I definitely am curious as to why.
Here is a bit of further explanation on a few of the questions posed. I'm really not sure how dead set I am on doing tournaments. I really enjoy skiing behind my boat on my lake with my peeps, so I may never do a tournament. Would this change your advice to maybe match more closely with @waternut and @gregy such that maybe I should just get to 30 or 32 and start reducing rope length even though I'm only 32 years old? Maybe especially since I'm on a ski that's slightly too large?
The ski is indeed currently a bit large. I bought it at a time when I was 185 and not super confident that I wasn't headed straight to 200. I also wasn't skiing well at the time on my old smaller ski, so I wanted something that wasn't going to be dragging like crazy if I could only run the course at 28 and was sitting at 200 pounds. I figure if I can get my weight back down to 160 where it should be and if I'm consistently running 34 mph, maybe that will be my perfect excuse to reward myself with a new smaller, maybe even more aggressive ski. I understand that I'm still in the age group for 36 mph, but honestly, I think I'm over it. I don't really plan on skiing at 36 mph ever again. If that means I have to wait 3 years before participating in tournaments, then so be it.
I'll get video up as well for sure. It was just me and him last week, and I don't have a rig for the pylon or anything, but as soon as we can get an observer in the boat, I'll post that as well as a picture is worth a thousand words and a video is worth a million. Thanks also for help with him. He won't be buying his own smaller ski any time soon, I'm sure, but we'll leave him on mine, and shorten his rope, and then have him start shadowing in reverse order like you mentioned. That seems like a decent way to progress from Jr. buoys to real buoys.
Thanks again everybody and please keep the suggestions coming.