Shade - The Rogue
Here is a sample backgound for Shade that will answer a few of your questions Mark. This was written for a character in my own game, but it can give you an idea about what I would like for this guy. I have no problem with changing anything or all of it to better fit the setting.
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Born into a poor family of four, Arim’s father, Gale Dupree, was a hearder of sheep and a skilled woodsman. His brother, Darren, was only a year older than Arim. The two brothers were raised to take over the farm when they grew older. They were taught how to raise sheep and how to hunt for food.
Unfortunatly, neither boy was happy with such a boring future. The village of Willowbrook was only a few miles down the road, and there was plenty to do there. When the boys got their chores done, they would go to the village and try to find a bit of excitement.
When Arim was fifteen he fell in with a bad group. Two other boys, about their same age, were known trouble makers. They taught Arim and Darren how to steal to get what they wanted. Starting as a fun and daring sport, it soon became a bit more serious. They began breaking into houses and shops and taking more expensive things than pies and apples.
When he was nineteen, the boys were caught. All of them managed to get away except for Arim. He was publicly whipped and spent a month in jail. When he finally got back home, his life was made miserable. His father double his chores, and the only freedom he got to enjoy was in the woods near his home or when he could sneak off to Willowbrook.
About a six months ago, the first of a number of hobgoblins came into the area. They began attacking farms and steeling livestock. Soon the village began to orginize it’s militia. Wanting to join the guard, Arim was made to stay and work on the farm while Darren was allowed to go. About a month after leaving, Darren was killed in an ambush. From that point on, the hobgoblin attacks started becoming worse.
While able to narrowly escape, the Dupree family’s house was burned and their farm destroyed. They moved to Willowbrook where Angela, Arim’s mother, is working at the temple to feed others who have suffered a similar fate. Gale is learning to be a carpenter and is working on the town’s defenses. He can’t be a member of the guard because of an injured knee he received from stepping in a hole. He is also working on the village’s communal farm and the family is staying in the Weary Eye Inn.
Arim has joined the guard and has recently been going out on scouting patrols. The patrols hunt down and kill any hobgoblins that happen to be traveling in small numbers. He has gained a reputation of being a talented warrior and being very quiet as he stalks his querry. This, along with a recently acquired dark sense of humor, has earned him the nickname Shade, by his peers.
As you can tell from my background, I may multiclass into a Ranger at 2nd level. By 3rd level, he'll be duel-wielding two Finessed short swords and be kicking goblinoid butt!
I think it would be easy to say he met the other characters while on patrol. Maybe they were all asigned militia duty together. *shrugs* Course, he grew up near the town so maybe he has known them since he was young.