Demoralizing is almost a 100% success chance at high levels as the DC of this check is just equal to 10 + the target’s Hit Dice + the target’s Wisdom modifier.
E.g. Lv11 with 11 skill pts + 3(class skill) = Total 14
BBEG at 2 levels higher with +2 wis mod = DC 10+13+2=25
You need to beat DC25 with a dice roll of 11 without any skill focus.
With skill focus(6), circlet of persuasion(3), masterwork tool(2) and maybe half-orc racial trait(2), that is 13 points more. Not even factoring in charisma mod.
You can't even fail on a 1 anymore, a -5 penalty can hardly be felt.
I have a build in mind that uses Cornugon Smash and Hurtful along with the Thug Rogue archetype.
By the time the build hits mid-levels it will be able to toss out as many as 3 Demoralize checks a round. I'm looking for some way of giving the build longevity so that by the second round the penalties aren't insurmountable.