Roughly, I'm aiming for something about as complicated as Circles.
- Easily traversed (farm and pasture lands) —
- Some challenge (open plains but adverse weather (wind, lack of water, etc); river country; foothills): +1Ob
- Challenging terrain (forest, tundra, high desert, marshy): +2Ob
- Very challenging (mountains, dune desert, swamp land, arctic): +4Ob
- Specific/rare/unique: +3Ob (or varies)
- Autumn —
- Summer: +1Ob
- Spring: +3Ob (Consider Health checks as well)
- Winter: +4Ob (Consider Health checks as well)
- Short trip: —
- Medium trip - 1 to 2 weeks: +1Ob
- Long tirp - Month or more: +3Ob (Consider Health check as well)
- Imperial highway: —
- "Passes for a road in these parts": +1Ob
- Traveler's trails: +2Ob
- Blazing a new trail: +3 or +4?
Rate of Travel
- Normal: (taking your time/Carefully should use the appropriate rules in the BWR) —
- Push to reduce time by 1/4: +2Ob (plus a Health test)
- Push to reduce time by 1/2: +4Ob (plus a Health test)
- Comfortable but not excessive/Ample forage —
- Traveling light: -1Ob if trying to travel fast, but +1Ob to Traveling Fast Health check
- Barren terrain: - no forage +1Ob (Consider Health checks as well)
- Extra provisions: +1Ob if traveling fast, -1Ob for any Health checks or 'traveling' checks if not traveling quickly, +2Ob for preparatory resource checks (provisions/beast of burden)
- Mounts/Wagons: -1Ob if trying to travel fast, +1Ob preparatory resources check, +1 die for Health checks
- Bandits (should be commonly added to good roads and highways) +1Ob to avoid -- no change if you don't care if you avoid them
- Predators (Around traveler's trails or blazing a new trail) +1Ob to avoid -- no change if you don't care
- Tolls/Taxes +1Ob to avoid, Resources check if ignored, based on size of group/mounts/beasts of burden
Examples: If you break the trip up into, say, three legs of the journey...
- A short trip through open farmlands, on open highways, in Spring, avoiding tolls at various crossroads, traveling somewhat fast (reduce time by 1/4), with mounts: Ob6, plus a health check for the mounts (animal handling/riding can Help). A failed roll would mean a run-in with the toll-keepers, or maybe a Health check for the rainy, cool Spring weather (Health checks with +1 Die bonus thanks to mounts). Also: a +1Ob to the preparatory Resource check, for the mounts.
- A mid-length trip through the baronies ("passes for a road"), still in Spring, with Mounts, some Bandit problems to avoid, toll-keepers at villages that will need to be paid: Ob7, plus a Resources check: tolls based on people + mounts, so fairly tough: maybe Ob4 or something. Failure would mean some bandits, greedy tax-men, et cetera.
- A long trip through orc-infested mountains in the Summer (Barren terrain, Traveler's trails): Ob13 (!!!), Health checks with +1 Die for mounts. Failure would mean orcs, natural hazards (avalanche of stone or snow), increased travel times, possibly pushing you into Autumn, and any number of odd encounters.
((Worth noting that these are probably unnecessarily complex challenges -- for lower-power games it would be enough to say "short trip, rainy spring, avoid Bandits -- Ob5", and add complexity when the campaign itself gets more complex -- I'd trot out ALL the difficulties when you're trying move platoons and the like.))
What skill do you test?
Eh. All of em?
Maybe Orienteering for more wild areas, Cartography for the well-traveled areas. The key bit would be the Helping skills and FoRKs, because pretty much everyone should be able (and want) to help with something -- off the top of my head, related skills would be:
- Any one of dozens of possible -wises.
- Animal Handling/Husbandry
If you're dealing with moving large groups, then you're talking about helping with Command and the like as well.
Resource checks with tax-men would also involve the bribery rules and such, and there's probably some bonus dice that could be had from smart purchases prior to the trip.
The way I see it (and the reason those Obs can be so high), the whole group kicking on on these test with Helping dice (and, as a result, getting checks on their skills).