Previously I whipped up a demonstration that the “classic D&D party” (Cleric-Fighter-Rogue-Wizard) can cover the skill spread quite easily. With the Player’s Handbook 2 out today, it is now possible to make a couple of power-source-themed adventuring parties, with all four party roles covered but without having to mix your peanut butter and your chocolate. There’s no reason to avoid such delicious flavor combinations, but sometimes you just want chocolate, right?

What we find, pretty quickly, is that there is a lot of overlap in each power-source group. The Arcanists all have Arcana, History, and Insight. The Divine classes all have Religion. The Primal classes all have Athletics, Heal, Nature, and Perception. Some of this overlap is reinforced by requiring characters to train spefici skills as part of character creation (Arcana, Religion, and Nature being the big culprits for obvious reasons).

With the exception of the Bard (which has every skill available save Endurance, Stealth, and Thievery), each of these groupings have big gaping holes in skill availability. If you want to have a broadly-skilled Divine adventuring party, you will probably have to sink a fair number of feats into skill training, or resort to creating a gang of Eladrin.

Moral of the story: mix up your power sources. Most DMs and players have been stitching together traveling-circus hodgepodges of adventuring parties for years, of course.

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In Dungeons & Dragons, not all skills were created equal. Each is intended to be of moderately-equivalent value to a player character, so that there are no completely-wrong choices to be made at that phase of character creation. Sadly, this isn’t entirely true. Of the skills presented in the Player’s Handbook, some stand out simply by virtue of their availability:

Acrobatics, Bluff, Nature, Perception, Stealth, and Thievery are all only available to two classes. For each of these (aside from Nature), the only classes that have the skill available fill the “striker” role in a party. In a typical four or five-character adventuring party, you probably won’t have more than one or two characters filling the same role, so failing to train one of these skills would leave your party short a potentially-valuable skill.

By contrast, Heal, History, Insight, and Intimidate are available to five classes each. It would be difficult to put together an effective multiple-role party without having every one of these skills available. These, then, would be good skills to just presume a party is going to be reasonably good at. E.g. out of five player characters three or four of them probably have Heal available, and one or two of them probably have it trained. This makes placing a somewhat difficult Heal DC into an adventure a pretty darned reasonable thing for a DM to do.

What should we take away from this? If you’re a player, kindly make sure you’re covering the skills your party needs you to be covering; you cannot expect your Wizard to be intimidating any more than you should expect your Paladin to be sneaky. If you’re a DM concocting a clever skill challenge, try to think of ways that the more commonly-available skills may come in handy, and whether you should set the bar high or low.
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After waxing mathematic on my wariness of the 4th Edition D&D skill challenge system, I ran across the DMG Errata. Oh look, they totally retooled the target numbers, number of failures, etc. Because there are so many changes, I’ll just put the relevant, updated text below:

What level is the challenge? What is the challenge’s complexity?

Choose a grade of complexity, from 1 to 5 (1 being simple, 5 being complex).

SKILLCHALLENGE COMPLEXITY

Complexity	Successes	Failures
1	4	3
2	6	3
3	8	3
4	10	3
5	12	3

Level and complexity determine how hard the challenge is for your characters to overcome. The skill challenge’s level determines the DC of the skill checks involved, while the grade of complexity determines how many successes the characters need to overcome the challenge, and how many failures end the challenge. The more complex a challenge, the more skill checks are required.

For an easier or a harder challenge, use DCs from the row that corresponds to a lower or a higher level, and assign the challenge’s level as the midpoint of that level range. For example, if designing an easier challenge for an 8th-level party, you could use the DCs from the “Level 4–6” row. That would adjust the challenge’s level to 5th.

Set a level for the challenge and DCs for the checks involved. As a starting point, set the level of the challenge to the level of the party, and use moderate DCs for the skill checks (see the Difficulty Class and Damage by Level table on page 42).

Example: A complexity 3 challenge using hard DCs and cutting the number of failures needed in half increases this skill challenge’s level by four.

This modification, along with a revised pg42 Difficulty Class table (effectively reducing the difficulty of skill checks by 10), means that the death spiral of skill challenge futility now points in the opposite direction: characters that excel at a set of skills related to a challenge now stand an excellent chance of succeeding. The math now looks an awful lot more like “roll some dice, feel good about training a couple of skills, win” instead of “roll some dice, curse your dice, throw your dice at the DM, curse a lot, fail.” Probably a good thing, though they may have swung things a bit too far over.