Regiment generation is going to be difficult as we will all pull in different directions. One way to handle it is to keep things deliberately vague and let it be filled in by each post one player at a time. This way its lore will grow organically instead of having one guy generate it at the beginning in a flurry of creativity which then dies out slowly throughout the course of the game. Remember, some things are more like rumors rather than facts. And if someone wants to, say, play a musclehead that doesnt mean the whole regiment has to be like him. In some ways he shines better alone.