Re: Sink hole
"Perhaps any would-be ambushers would be less inclined to risk life and limb if we readied our weapons and complained frequently about how broke we are," Jake wonders aloud as he takes out one of his daggers, "I will defer to your greater wisdom if you decide that it is worthwhile to go off-road, but I'll admit a reluctance to try it. Even if I could keep up with you, progress would likely be four times as slow and it's unlikely I'd be in any condition to back you up effectively if we wound up attacked."
The road is windy and steep, but passable. The surrounding terrain is steeper and riddled with loose rock and thorn bushes, but also still passable.
((In game terms, think level appropriate Endurance and Athletics skill challenge where success means 1/2 the chance of random encounter in exchange for 1/2 overland speed. Failure = lose healing surge and 1/3 overland speed or some such. Meta tip: Ambush not inevitable, but possible. Arrival time at destination will matter.))