I think the bear is really helpful in the White Way, Wong Way quest, but I prefer just having a boat-load of gunslingers/deputies. You can have more than 3 deputies if you build additional Sheriffs Stations. Likewise, you can hire additional gunslingers by building additional Saloons. If you're strapped for cash, try fighting some of the bad guys up in the North with your Hero. They usually drop gold and since your Hero can't die, it's like free money. Or, you can try completing the other side quests, such as the Outpost missions. You also might want to get the Blacksmith and Gun upgrade.
@Charis: The Bakery quest came before the White Way, Wong Way quest for me. Perhaps you missed it?
I'll post more about beehives and bears in the Strategy section here.