3) Roles are sorted out as follows:
* The Cleric/Warlord will Quartermaster (folding Make Camp/Forage/Manage Provisions into one) as this involves steadying the nerves and fortitude of allies.
* The Ranger/Cleric will Navigate as (a) he knows the way, (b) can handle the horses if they get spooked, and (c) it allows multitasking to take inventory of the surrounding paranormal climate (aberrant or shadow).
* The Rogue will Scout Ahead as much of the character's life has been "head on a swivel", (s)he has a sixth sense for detecting danger and things amiss.
* The Warlock will anchor the Group Endurance Check of Take Watch with physical and arcane fortitude born on the back of his patron.
4) Resolution:
Quartermaster succeeds at their Diplomacy, Insight, or Heal
Navigator succeeds at their Nature
Scout succeeds at their Stealth
Despite the Warlock succeeding at their Endurance and an Endurance Secondary Skill to buff a low Endurance by the Rogue, the other 3 PCs fail.
So we have a Take Watch complication that needs to put some adversity into the collective face of the PCs.
Excellent! And probably not too different from how this might actually play out at our table.
I've been giving thought to how character Skills might be applied to the roles,
Quartermaster,
Navigate,
Scout Ahead, and
Take Watch (or its variant here, which I like very much). I don't like to limit player creativity (one of many problems with prescripted SCs, in my opinion), but I do hope to avoid situations like "Intimidating the grass." (I don't think this is a real risk in my group, but....)
Quartermaster: Dungeoneering (underground), Endurance, Heal, Nature (outdoors) seem obvious choices to me. I am intrigued by your inclusion of Diplomacy and Insight in the example. (This is not to argue against them but rather to invite further discussion of how you see their utility playing out.)
Navigate: Arcana (tapping into ley lines), Dungeoneering (underground), Insight, Nature (outdoors), Perception seem like the go-to Skills here.
Scout Ahead: Acrobatics, Athletics, Dungeoneering (underground), Endurance, Insight, Nature (outdoors), Perception, Stealth, seem candidates here.
Take Watch: Arcana (magical wards), Endurance, Perception, Religion (consecrate grounds) would be a good fit here.
Thoughts? Again, I would like to leave as much room for player creativity as possible but also would like to present options to help spark that creativity.