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Having spent hours upon hours trying to design fun, interesting skill challenges based on the situations I've put my players in I've decided to start from the other direction, by creating a better formalized framework for creating skill challenges. This is still a work in progress (though I've got something I can start playtesting at least) and I don't expect it to be everyone's cup of tea, but for me I think this will get me closer to the point where designing an interesting skill challenge doesn't take much more effort than designing a fun combat encounter where you pretty much just choose a few monsters and set some terrain.

For combat encounters this works so well because the combat system itself provides tactical challenges and creates interesting choices which the character and monster powers can play off of, so my goal is to create a similar system for skill challenges by making the fundamental system about something more than just making skill checks and counting successes.

Details are on my blog, but I can repost them here if desired. I would very much like to hear your comments.

Good luck.

Reposting here from my blog:

Work on the skill challenge system for 4E sketched out in previous posts is progressing, though more slowly than I'd like. Actual gaming (primarily Rift, The Lord of the Rings LCG and Dominion on Isotropic) has distracted me... a pleasant distraction, but a distraction nonetheless. I have started committing my ideas to paper and the structure and terminiology is pretty much settled though some things are still in flux. Playtesting is still needed - I had hoped to do a test run with my regular 4E group during the weekend but the session got canceled due to outside influences in the form of birthdays and moving woes.

In the meantime I'm going to present a sample skill challenge. Hopefully a concrete example will help anyone interested in this see what I'm getting at. Note that some numbers haven't been set - I need to do more playtesting before I know where they end up. Also note that this post does not contain explanations for how everything works or what the terms mean. This is meant to give an impression of what kind of things the structure I'm working on will allow you to create.

Sample Skill Challenge: The War
A war is brewing and the characters have been put in charge of raising an army and marching it to the Evil Nation to defeat the Big Bad's legions.

This challenge consists of a sequence of three scenes: Raising the Army, The March and The Final Battle.

Scene 1: Raising the Army
The characters have to raise an army for the Good Nation. This will involve recruiting and training troops as well as negotiating alliances with bordering nations and the mountain tribes. Note that this is a no-fail scene, but if the players take too long to complete it they will have a harder time later on.

Main Track: Raise and Organize Troops
Medium
When this track is completed, the scene is over. Failures generate setback.
Primary skills: Diplomacy, History (easy)
Secondary skills: Bluff (risky), Insight, Intimidate (volatile)

Hindrance: Enemy spies
Medium aggressor
Primary skills: Bluff, Stealth, Streetwise
Secondary skills: Insight (hard), Intimidate (risky)
Targets: Bluff, Insight, Streetwise

Side Track: Forge Alliances With Border Nations
Short
When this track has been completed all rolls on the primary track gain a +3 effect bonus. From turn four onwards all skill rolls suffer a -2 penalty if this track has not been completed. The penalty is increased to -3 if this track is failed.
Primary skills: Diplomacy, History, Insight (hard)
Secondary skills: Bluff (risky), Intimidate (volatile)

Side Track: Ally With Mountain Clans
Short
Until this track is completed all skill rolls on the primary track suffer a -2 penalty. (It's hard to raise troops for a foreign war while the clansmen are raiding.) Completion also gives bonuses in later scenes as noted below.
Primary skills: Diplomacy (hard), Insight, Intimidate
Secondary skills: History, Religion

Hindrance: Clan Customs
Minor barrier
Primary skills: Athletics, History (hard, risky), Insight
Secondary skills: Acrobatics, Bluff, Endurance
Targets: Athletics, Endurance, Insight

Side Track: Training the Troops
Medium
Successfully completing this track gives bonuses in later scenes as noted below. Failure generates setback.
Primary skills: Athletics, History, Intimidate
Secondary skills: Endurance, Insight

Hindrance: Limited Equipment
Medium barrier
Primary skills: Bluff (risky), Diplomacy (easy), History
Secondary skills: Athletics, Insight, Intimidate (volatile)
Targets: Athletics, History, Intimidate

Hindrance: Language Difficulties
This hindrance activates when the Forge Alliances side track is completed.
Minor distraction
Primary skills: History (easy), Insight
Secondary skills: Bluff, Diplomacy
Targets: Diplomacy, History, Insight

Hindrance: Old Enmities
This hindrance activates when the Ally With Mountain Clans side track is completed.
Minor aggressor
Primary skills: Insight, Intimidate
Secondary skills: Athletics, Diplomacy, History
Targets: Diplomacy, Insight, Intimidate

Scene 2: The March
The army is now on the move, forcing its way into the Evil Nation.

Main Track: Maneuvering for Battle
Medium
When this track is completed the scene is over. Failures generate setback. If the Training the Troops secondary track was successfully completed, all success rolls on this track receive a +1 bonus.
Primary skills: History, Intimidate, Insight, Bluff (risky)
Secondary skills: Diplomacy, Endurance

Hindrance: Unfamiliar Terrain
Minor distraction
Primary skills: History (hard), Nature
Secondary skills: Endurance, Perception
Targets: History, Nature, Perception

Hindrance: Minor Battle
Medium barrier
This hindrance activates when half the main track has been completed.
Primary skills: History, Insight, Intimidate
Secondary skills: Arcana, Athletics, Endurance, Heal, Religion
Targets: Athletics, Endurance, Insight

Side Track: Lead Scouting Parties
Short
All checks on this track gain a +2 bonus to success and progress rolls if the Ally With Mountain Clans track was successfully completed. Successfully completing this track removes the Unfamiliar Terrain hindrance from the main track and gives a +2 bonus on skill and effect rolls for the Supplies secondary track.
Primary skills: Nature, Perception, Stealth
Secondary skills: Athletics, Endurance, Insight

Hindrance: Hostile Patrols
Medium guardian
Primary skills: Bluff, Perception, Stealth
Secondary skills: Athletics, Insight, Nature
Targets: Bluff, Percpetion, Stealth

Side Track: Supplies
Medium balance
This track suffers a minor setback each turn. While it is negative all rolls on the primary track suffer a -2 penalty to skill and effect rolls.
Primary skills: History, Intimidate, Nature (hard)
Secondary skills: Bluff, Diplomacy, Insight

Scene 3: The Battle
The characters' army joins battle with the forces of evil.

If the party took more than five turns to complete the main track in the first scene they have a -1 penalty to all success rolls in this scene.

Main Track: Directing the Battle
Successfully completing this track leads to the Final Confrontation combat encounter, while failure leads to the Fleeing the Battle combat encounter.
Medium
Primary skills: History, Insight, Intimidate
Secondary skills: Bluff, Endurance

Hindrance: Enemy Maneuver
This hindrance starts in play and is renewed after one third of the main track has been completed and again after two thirds.
Medium puzzle
Primary skills: History, Insight, Perception
Secondary skills: Bluff (risky), Intimidate
Targets: Bluff, History, Insight

Hindrance: Undead Legions
Medium distraction
Primary skills: Intimidate, Religion
Secondary skills: Arcana, Insight
Targets: Insight, Intimidate, Religion

Hindrance: Enemy Charge
This hindrance enters play after half the main track has been completed.
Major aggressor
Primary skills: Athletics, Endurance, Intimidate
Secondary skills: Bluff, Insight
Targets: Athletics, Endurance, Insight

Side Track: Neutralize Enemy Spellcasters
Until this track is completed all rolls on the main track suffer a -2 penalty to success and effect rolls.
Short
Primary skills: Arcana, Stealth
Secondary skills: Bluff, Insight, Perception

Hindrance: Illusions
Minor barrier
Primary skills: Arcana, Insight
Secondary skills: Perception
Targets: Arcana, Insight, Perception

Side Track: Lead Counter-Charge
This track activates when the Enemy Charge hindrance on the main track has been defeated. If it is successfully completed all success rolls on the primary track gain a +2 bonus. All success rolls on this track gain a +2 bonus for each of the Ally With Mountain Clans and Training the Troops tracks that were successfully completed.
Medium
Primary skills: Athletics, Endurance, Intimidate
Secondary skills: Nature

Side Track: Maintain Morale
Balance
While this track is negative, all success and effect rolls on other tracks suffer a -2 penalty. This track suffers a minor setback each turn, or a major setback while the Undead Legions hindrance is in play. If the Training the Troops track was successfully completed all checks on this track receive a +2 bonus to success and effect rolls.
Primary skills: Bluff (risky), Intimidate (risky), Religion
Secondary skills: Insight