The thief skills where a mess. I remember back when one book at thief skills for low levels; when they came out with the next book, they retroactively made lower level thieves worse, to give room for higher percentages.
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A method I've played with to make percentages less clunky is to always roll two d10s. Then you get 5 levels of success:
Botch: Doubles, over the target %.
Failure: Reading the dice both ways is over the target %.
Success: Reading the dice one way or the other is under the target %.
Masterful: Reading the dice both ways is under the target %.
Critical Success: Doubles, under the target %. 00 is always a critical (it is a "roll of 0" not 100).
Skill | Botch | Failure | Success | Masterful | Critical |
10% | 9% | 72% | 18% | 0% | 1% |
20% | 8% | 56% | 32% | 2% | 2% |
30% | 7% | 42% | 42% | 6% | 3% |
40% | 6% | 30% | 48% | 12% | 4% |
50% | 5% | 20% | 50% | 20% | 5% |
60% | 4% | 12% | 48% | 30% | 6% |
70% | 3% | 6% | 42% | 42% | 7% |
80% | 2% | 2% | 32% | 56% | 8% |
90% | 1% | 0% | 18% | 72% | 9% |
This lets DM's say "just don't botch", or "Regular success" or "Masterful", or "Only on a critical".
Low skill% get Successes pretty quickly. For reliable Masterful rolls, you need a chance well over 50%.
Every +10% skill gives you 1% more Crit, 1% less Botch. If you count a Botch as -1, a Failure as 0, a Success as 1, a Masterful as 2 and a Critical as 3, then each 10% skill "earns" you an average improvement of 0.2 "points" per attempt.
Toss that at the old-school thief check tables, and I strongly suspect you'd end up with much less comical lower level thieves (they wouldn't do things masterfully), and higher level thieves would start being able to pull off masterful things.
(Mathematically, this is really similar to rolling twice, or an advantage/disadvantage system. But with percentiles. Failure means "would fail even with advantage", Success is "would succeed with advantage", Masterful is "would succeed even with disadvantage". But I find it is much faster to glance at 2d10 and see if both/neither/one is under your skill % than it is to do advantage/disadvantage d20 math).