|Jeremy Mac Donald|
I'm not exactly sure how that would work. Though I suppose if you optomise a monster often what your really doing is fiddling with it in order to make it either better at hitting your players weak points or better at mitigating their strengths.
In that sense I suppose that DMs might set skill challenge DCs not by the book but based on their PCs actual skills. This has, so far as I can see, a strong point in its favour and a couple of points against.
In its favour you can set the DCs to be about 5 higher then the PC you judge most likely to utilize this skill in the Skill Challenge. Its actually at a DC of 5 higher that the numbers for a skill challenge work at their best.
Opposed we have...
#1: Extra work for the DM - instead of just putting a challenge together now the DM needs to review his players character sheets and make some reasonable estimates on who is likely to try and use which skills.
#2: Very inauthentic way of playing the game - If your players ever figure out what your doing it'll really feel like their choices don't really matter - especially things like skill training and skill focus feats, since improving in these areas can't help them if you just adjust the DCs to compensate.
In general I mainly can't see the game being worth the candle. In reality one wants to focus ones efforts with a skill challenge on making it run smoothly and be interesting. Optimizing monsters is about providing ones players better combats but most of the time I don't think playing with the numbers get you as far with a Skill Challenge as simply focusing on its make up and making sure that the scene the players are involved in during the Skill Challenge is compelling and memorable - one you have compelling and memorable then it usually does not matter one way or another if the PCs win or loose the Skill Challenge - its already accomplished its purpose of adding to the story.
I suppose my question would be... what do you mean by optimized?
With a PC, it is usually pretty simple to design - a character could be optimized for damage, or for making skill checks, or for durability, or for general overall effectiveness.
With monsters... at least in 4E, I don't usually see that sort of thing, since the monster creation rules are already intentionally somewhat open-ended. In 3rd Edition, you might have seen more of it, simply because there was a bit more encouragement to do things 'by the book' - so a DM might try and figure out how deadly a monster they could make by advancing hit dice, adding templates, etc.
4E tends to say, instead, "Look, if you want to add a new power to your monster... just go ahead and do so. But, like - try and do so because you think it is a cool power, not because you want to see it brutalize the PCs, ya know?"
And of course, you could do the same thing in 3rd Edition as well - that's where I tended to end up, adjusting monsters to be interesting rather than worrying about making them as lethal as possible, and designing more by feel than by formula.
A skill challenge falls into the same category. What are you optimizing it for? To make it harder for the PCs? My question would be... why? What's the purpose if it is designed for failure? And if you really do just legitimately want a super-hard Skill Challenge (say, as part of an optional sidequest or puzzle or the like)... you don't really need to 'optimize' it, so much as simply make it higher level or require more successes.
Of course, other sorts of optimization might be reasonable. For example, here is something I do with nearly every challenge I make - I optimize how many PCs can take part in it. A challenge that consists of reading a bunch of old books and making a handful of History and Arcana checks might be interesting to the party wizard and cleric, but boring to everyone else.
But if you discover some key books are missing, and so the rogue, ranger and fighter go track down whomever is holding onto the overdue books and intimidate them into giving them back?
Having some built-in options for different approaches, I've found, is a good part of making a skill challenge memorable and exciting for everyone. And so, yeah, some level of 'optimizing' takes place. But for me, that is mainly just part of the design - making it interesting is part of the default, rather than an occasional exception.
To have an optimized skill challenge, you probably need to look at some alternatives to the 4E system. Perform a google search on the obsidian skill challenge system, and that should be a good start. The only pitfall you want to avoid is a skill challenge with a dead end; if it fails, there is no way for the characters to proceed.
Beyond that, it is probably just preferences on how to run one.