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I know that at least some of this has been discussed before but the thread that I was following got locked.
The following is all based on theorycrafting from my first pass of the book. I'm really hoping to hear from people with actual play experience at mid to high levels that I'm missing something.
It seems to me that as one advances in level one basically gets worse at CR appropriate skill checks unless one is a specialist. The dilletante just gets worse and worse. Not much use for the soldier to even try being a diplomat.
That "Difficulty = 15 + CR * 1.5" thing looks like it means that most characters just can't keep up. The specialist can just about keep up with that but only by spending lots of resources.
So, at 1st level, a non specialist has something like Stat +2, Class Skill +3, 1 rank. +6 vs a DC of 16. Not bad.
At level 11, that same specialist has something like Stat +4, Class Skill +3, 11 ranks, maybe a +2 stat boost item, for +19. Vs a DC of 37.
Pretty bad. May succeed but not likely to.
On the bright side, for whatever reason, bluff does NOT follow this progression. So, my soldier can bull$#$% effectively through his career :-). Just not make nice.