Hey guys...
Our horse journey heading towards the monastery is going to be the start of a Skill Challenge. Let me quickly go over how I am running it, so you all know how you each want to roleplay it.
This particular Challenge requires 4 successes before 3 failure. Each skill check will occur as follows. I am going to write out a small section of the journey, with some sort of obstacle or incident occuring. At the end of the rp, there will be a list of 3 skills that are applicable to use to get around/through the particular incident. The DCs of the 3 skills will be secret to you (but will be either DC 5, 10, or 15). All six of you will choose one of three skills to make your check with, and your roleplay of what happens as you approach/deal with the incident should reflect which skill you are using. I leave it up to you all to bring a cohesion to the story (so that if someone posts some methodology in the first rp, each subsequent person should build and extend the stories from there, rather than completely split away and do something completely counter to what was set up previous).
To gain 1 success, three of the five of you must succeed in the skill check you chose for yourself. The 6th person will not have a direct influence on the success/failure... but rather, he will be allowed to "Aid Another" by making one of the skill checks at an automatic DC 10 (regardless of what the hidden DC is for that particular skill). If successful, he can add a +2 to another player's skill roll that matches the skill he made his Aid Another check in.
Thus, you guys can all discuss and strategize here in the OOC which one of the six of you will make the Aid Another check, and who will be the recipient of the +2 should he succeed. It'll take a little tactical thinking on all your parts in deciding whether the characters who have very low skill mods in all three skills being used should be the one to roll the Aid Another at the straight +10 (since you know the DC already and there's no penalty for failing the Aid Another roll), or whether they should be the recipient of the +2 (plus hoping that the skill they chose might be a DC 5 for that check).
Some thing to bear in mind: Although the possible DCs will be 5/10/15 (easy, moderate, difficult as per the DMG errata for 1-3 level characters), not every set of the 3 skills will necessarily have one of each. Some checks might have two DC 5s and a 15, one might have a DC 10 and two 15s, etc.)
Also... in each "section", individual character successes or failures will have no party consequences. I am only looking at the complete set of rolls and whether 3 of 5 were successful. It is these party-wide successes or failures which will give you small benefits or penalties throughout the rest of the Skill Challenge (and possibly beyond it). This might include things like bonuses or penalties to subsequent skill checks, loss of one or more Healing Surges, getting into combat, monetary awards, et al.
And as I mentioned above, the ultimate success or failure of the Skill Challenge will be 4 of 7 party successes. If the party fails the entire challenge, then a larger penalty will be in effect (and of course the loss of the XP you would have gained for succeeding in the challenge).
Any questions about this, please feel free to give them here, and I'll do my best to answer them. Thanx all!