Should a GM increase a skill challenge's difficulty if two PCs have obscenely high skills for it? Or should he keep it moderate and give the players a "freebie" to reward their specialization? I was kind of leaning towards the former, but a player gave me a cynical outlook on the whole thing: "It doesn't matter how much you optimize, the GM will just raise the challenge to compensate, so why bother?" I can see players getting frustrated if they're continually failing skill checks they invested in because the GM raised the DC in response. What do you think?