@Jordan - I think there is definitely something to be said for not constantly changing things. I think this is particularly true in a sport like waterskiing, where our opportunities to practice are so limited. Even if you have a situation where you can ski as much as you want, your body can only take so much. If I play basketball, I can go to the gym and shoot 1,000 free throws in under 3 hrs (I looked it up lol), and I could do that every day, even twice a day! As a skier, we only take 12-20 passes in a practice session (generally speaking), and at least personally I can't keep that up 7 days a week.
At this point, any high-end ski is a good ski, so if you're on a high-end ski, even if new Ski XYZ is a little bit better, you're also going to use valuable practice time adjusting to the ski. And even if your old Ski ABC isn't quite as good, if you know exactly what to do on it, you may ski more buoys than on a "better" ski that you aren't as familiar with.
That said... obviously this doesn't mean you never upgrade a ski! My skis have been the '16 Radar Vapor and the '22 Radar Vapor, and from my first pass the '22 was a noticeable improvement. I think I'm pretty committed to Radar now in part because the skis continually evolve from their previous iterations, so I suspect there would be less adjustment time needed to keep upgrading to new Vapors as opposed to switching between brands every time. I figure, I get the excitement and improvement of new gear (I'm with you there as a gearhead!) but it feels more like just "an improvement" as opposed to "a change and improvement." Not that this is restricted to only Radar, this sort of thinking would suggest finding "your preferred brand" and then upgrading only within their offerings.
That said... the only other ski I've even tried is a C85, and I'm a 34mph, 15-28off skier, so I'm curious if someone who has more experience skiing and more experience trying various brands and models would agree with or refute my theory!