I liken this to the AK vs. AR argument. My solution, get both and enjoy each for what it is. Sure there is the argument that if you train with both, you will never be as good as you could if you only trained with one platform.
I grew up and learned to ski behind a 19-foot 69 Hallett V-drive V-bottom on Lake Tahoe. Sure it was a lot small for Tahoe, especially in the white caps. I remember that that thing rode really nice and was relatively fast for the cement mixer BBC that it had in it. Yes, it had a cramped interior compared to a jet or an I/O. It did have a Casale “crash box” (with reverse), but we never used the reverse. The owner said it was best to just stop the engine before shifting into reverse. IMO, the Powerglide is the way to go. I have been involved with a few V-drives that have used TH400 with 1st gear removed. The before mentioned 69 Hallett, at one time, had a TH400 and the owner said that 1st was useless. 2nd gear was used for taking up slack in the ski ropes and reverse was used instead of shifting the Casale. I would consider a Lenco reverser.
As with any boat, routine maintenance is the key to longevity. Contrary to popular belief, jets actually do require routine inspection and maintenance. Just because a V-drive is slightly more complex than a jet, that shouldn’t put you off. I was intimately involved in the repair and maintenance of my friend’s 69 Hallett, mainly because I was eager and loved to wrench on it. The most common failure was the water pump impeller getting chewed up. As far as the Casale, it is just a few bearings and gears. Much simpler than a manual transmission which have proven themselves reliable for many tens of thousands of miles all while being neglected. If you go the auto tranny route, the longevity there will be comparable or even more so than a road vehicle as the main source of heat, the torque converter, is eliminated and only a small heat exchanger is required.
As far as the complexity of the rigging, do you really need the capability of a K-boat? If your primary goals are “All I want to do is put to a beach and make do some hot laps towards the end of the day” you can get away with a basic shifter on your trim plates similar to a manual Place Diverter. That is all that 69 Hallett had, actually they never even shifted it. I have even seen several boats rigged with no trim adjustment at all beyond just the turn buckles. How is that for simplicity?