Finally tried my hand at some math for my proposal above. I'm not a mathematician, so I might be wrong on this, but I think it might be right, or at least fairly close. Anyway, here it is:
12th level Monk with 20 Dex, 18 Wis, +9 to hit, 1d8+5 damage, Save DC 16. Opponent AC 17, Con save +5.
If...