I use a house rule that makes the transition from 20Wanything to 1Wanything+1 to be more "significant" than other transitions. (I think someone else on this list actually recommended this a year ago or so.)
So when Croly the Rass campaign Shaman was at 20W2 in Tradition knowledge, I didn't let him raise it after adventures that were "run of the mill" examples of his using his shamanic skills.
By the same token, slashing through 188 skill 17 warriors doesn't necessarily give a Death Lord a new insight that allows him to move up to a new mastery.
Of course, this just forces the characters to either save HP or spend points on rounding their characters, but neither of those are bad things. And it makes the characters start looking for something Big to do, as they should.
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