My Greyhawk cowboy character is somewhat different from what you're going for; he's a Wil Rogers type Bard (free whip proficiency) singing the cows to sleep at night--a Baklunish Paynim tribesman with maxed Skills in Profession(herdsman) and Ride.
His main goal is increasing his herd size. Finding gold to do so is his main motivation for adventure, and finding exotic, valuable herd animals is his motivation for traveling outside the Paynims.
His favorite weapon is the longhorn stampede--1d12 for every 5 longhorns in the stampede.(as per Monster Manual/Animal/Bison) Remember in the Jungle Book how Mogli killed his nemesis by stampeding his herd into the gully where Shere Kahn was trapped.
I'm snagging your character; he could make a good ally or even maybe a future cohort. Thanks and have fun with him.
