It all depends on how gritty you want to make it...
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Originally Posted by coronatiger
Assume an "out-of-combat" situation, and that the total distance will be somewhere between 100 and 1000 meters. (We won't be doing second-by-second action.)
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So, cinematicaly non-gritty. Copy.
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How do I model running through difficult terrain in GURPS, like cluttered backyards, building sites or wrecked buildings?
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I usually just decide on a percentage of movement slowed each area might impose.
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1. How often should I require the players to roll?
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Once per 'time unit' you want to cover. Or distance unit? Whatever.
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2. Which skills should I allow/require? I'm thinking that Climbing, Jumping and Acrobatics are viable options, possibly Running. Are there other skills that could be used?
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Area Knowledge makes a good Complimentary Skill to the above.
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3. Should I assign different difficulty levels to each skill depending on the type of obstacles?
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Sure. A fence should be easier to Climb than Acrobatics over and Running is just not applicable (for instance).
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4. How do I determine how quickly the characters traverse the area?
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Calculate how long it would take to traverse the distance, then reduce the time taken as a percentage. Like -10%xMOS. Or -5%. Or whatever you think is good.
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5. How could familiarity with the terrain reduce time spent and/or difficulty?
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See above Area Knowledge Complimentary Skill mention.