This isn’t an answer to you *post* as much as your *title*...
Diving with contacts is no more annoying than contacts in the first place. My lenses are 10.0 or so and one is a toric lens on top of that. I’ve only dove with contacts, never a prescription mask.
It means I can’t open my eyes underwater, and I have to be careful clearing my mask to make sure it’s clear. I *have* had a contact pop out no more than 2-3 times in 500 dives (but never lost one!) and slosh around my eyes for a bit a few more times than that. I found the reason for that was almost always drops in my *eyelashes* getting in my eyes — I have fairly long lashes. If you’re careful, you can manage that pretty easily once you’re aware of the issue.
Diving with contacts has never limited my diving, including drills where I’ve had to swim 50’ at depth without a mask, and *bunches* of mask-off and replace drills.
I find contacts in a *pool* a zillion times harder to deal with: nobody’s ever tried splashing me unexpectedly while diving...
Why no prescription mask for me? I lose masks... and a backup pair of contacts is cheaper and a lot easier to manage — and covers more failures.