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This is why Intimidation is a floating skill at my table
(startrek.website)
Humor, jokes, memes about TTRPGs
There are abilities and gear that lower your crit requirement, but usually only by 1, so 5% higher chance of crit. I agree that your crit chance should go up as you get better, but only in relation to the skill of your opponent. Like I'm sure Bruce Lee could punch me exactly where he wants to 100% of the time, but not so much against Donny Yen. The pathfinder system sounds smart.
It's definitely possible for people who have mastered things to critically fail. How many times have you drunk water in your life? Millions of times? But every rare once in a while you mess it up so bad that you put water into your windpipe. That's a critical failure. But the chances of it happening when you've mastered something should certainly be far lower than 5%.
Conveniently, that's also how Pathfinder does it.
I can't remember when I last failed to drink. Maybe I'm an overgrown halfling and get to reroll 1s
I was going to mention the feats that change crits in DnD 5E but I felt that was getting too far into the weeds. The fact of the matter is you skill doesn't really matter for crits in 5E. Maybe you decrease the requirment for a crit by 1, but let's say you have that and great weapon master. Shouldn't that -5 to hit effect your chance to crit? You're going all in on power, so you lose precision. Why are the odds exactly the same? It just doesn't make sense. The crit system is half baked and doesn't really work, and then your throw in advantage and disadvantage and the system is really flawed. Pathfinder 2E seems to have figure this all out, but the new version of DnD (5.5E, or whatever they call it) doesn't seem to try to fix it.