i admit I had to reread this a few times before seeing where I could make a comment.
Here is what I would suggest about obstacle 1: it might be best represented as a complex obstacle, but a journey conflict might also suffice (i describe that in a second post).
Complex Obstacle: Travel from Lockhaven to Elmoss for delivery and pick-up; travel to Sprucetuck for delivery
The group will have a trek on their hands to handle travel during the cold fall rain. With their efforts dictating the possible life or death of many mice in Gilpledge, they are given the mission to travel to Elmoss to negotiate a one-time gift of moss to Gilpledge with little or no return.
The patrol must make the following tests in order:
Pathfind from Lockhaven to Elmoss - failure could indicate that the trip takes too long and the weather changes
Survivalist for encampments during the travel - failue results in mice taking sick, angry, or tired condition (sick falling to the mouse making the test and tired falling to helpers; angry falls to a non-helper that is unhappy with the poor encampments)
Health against the cold rain (or other weather) - failure results in mice taking the sick, tired, or hungry/thirsty condition (sick to those failing by higher margin than those failing by lesser margin)
Circles to find a helpful moss harvester or wholesaler - failure resulting in a linked resources test or a negotiation conflict
Those three tests cover the travel to Elmoss and gathering of moss. There is not much reason to ask much of the mice delivering mail except to narrate they have carried it and delivered it. Delivering mail might mean they must wait in town a short time to ensure all is distributed. Now that they have the moss (and conditions of any failed tests) they must make their way to Sprucetuck and negotiate a one-time medicine brewing gift for Gilpledge with little or no return.
The patrol must make the following checks in order:
Circles to find a helpful mouse herbalist or medicine brewer - failure may create a new enemy who is dissatisfied that the Guard seems to ask so often for free medicines for other cities
Haggler to form a barter for the brewing - failure may lead to a negotiation conflict to ensure the Guard will recompense the mice of Sprucetuck for their generous giving each year (you should expect that mice make promises during the conflict which should be binding)
Now the guard has completed a complex obstacle which very likely left some mice with conditions, created a new enemy (maybe more), and bound them to promises of compensation in two cities. They have acquired the moss and had it brewed into medicine. They are now prepared to travel to Gilpledge to deliver the medicine. If they have not been earning checks during these tests, shame on them.
Obstacle 2: A small cohort of bandits has come from nearby Dorigift where many other sick mice are now in need also
These badnits are from the nearby city of Dorigift, but the families of Dorigift have been sick only a few days. The illness spread easily between the two towns. These bandits counted on the Guard attempting to fulfill a request for aid from Gilpledge, but are intending to steal some medicine for their own families in Dorigift. The illness and desire to serve their own families has overcome their natural inclination to treat the Guardmice well. They have been watching for a good ambush point outside Dorigift to overtake the Guardmice travelling to Gilpledge.
They will initiate a fight conflict, but might be willing to hear out a negotiation conflict as long as the mice understand that it is to negotiate medicine for Dorigift also.
Immediately after the bandit obstacle is resolved, end the GMs turn. the players will need their checks for the following tasks yet unresolved:
- finish travel to Gilpledge (not quite as big a deal that a Pathfind Ob is needed, but a mouse needs to decide that the group must fulfill the original mission to Gilpledge)
- treat sick mice in Gilpledge (this could require two checks)
- Retread some steps to treat sick mice in Dorigift (the town is so nearby that a Pathfind Ob is unnecessary): If the treatment of sick mice in Gilpledge did not go well, there might not be any medicine left
- return to Sprucetuck for additional medicine (this might require a check to Pathfind and a check to Haggle, but I would not require checks to return from Sprucetuck)
- Any additional treatment needs (if they have acquired additional medicine)
- Pathfind to Appleloft or Lockhaven for oncoming winter
- finish the fall harvest in Gilpledge/Dorigift region
- possibly track bandits with stolen medicine (if the bandits got away with medicine, this will be an option)
I wouldn’t spend much time during the GMs turn to allow out-of-mission checks, but you might allow them a chance to voice ideas for preparation on this trip. Some examples might include, gathering winter cloaks or extra candles, negotiating hare mounts, gathering simple trade goods for barter. Each might provide a +1D for some of the upcoming tests.