Playtest Scenario
[OOC: Okay, since Oliver didn't really know the musket guy was hiding in ambush, we're going to treat this as a surprise round where everyone but Oliver can act.
Initiative order is:
Bandits 13
Oliver 11 (skipping due to surprise)
Lira 9
Callum 4]
The greedy bandit's eye follow the purse for a moment, but as soon as he spots Oliver trying to get off his horse, he fires instinctively. The shot goes wide, however, carving a sizzling divot into the dirt a few inches away from where Oliver crouches.
A second gunshot, more distant, rings out from the south, and Callum hears a musketball whiz past his head. The man on the bridge makes a shot as well, which unsurprisingly goes wide. There's silence for a moment, then a clatter of guns as the bandits largely abandon their spent weapons. Lira discharges her crossbow into the treeline to no effect, the bolt lost in the tangle of branches.
Callum, for his part, spurred his horse into a sprint, drew his saber, and tried to interpose himself between Oliver and the man in the hat. Oliver would still have time for his shot, however, as Callum had been a bit slow to react, and wouldn't be there in time to cut the bandit leader down.
The man in the hat pulled a worn-looking side-sword from a scabbard, charging forward to hack at Oliver. The rider on the bridge opened his horse up into a sprint as well, charging in Oliver's general direction. The brigand in the felt hat was still much closer, however, and he was about 20' away when Oliver saw his moment to take the shot... there was a loud crack of gunfire, but then nothing. The bandit leader continued charging at him; Oliver had missed!
[OOC: Don't forget to roll Pierce die and add AC to your hit rolls, but in this case a Pierce would only offer a +1 to the AC to bring to 19, still 1 short.]
Meanwhile, Lira saw the man hiding in the trees abandon all cover and all attempt at stealth, breaking from the trees and heading toward the road to assist his brothers-in-arms. He had no mount, but was moving at a dead sprint and fumbling to retrieve a pistol from his hip. He had managed to get about 20' away from Lira and her horse in the time before she'd be able to reload a bolt.
[Bandits 13 (already went)
Oliver 11 (already went, just went with your stated action of dismounting and shooting the leader)
Lira 9
Callum 4]