An outlaw gang who traveled in a wagon train full of women and kids would have lasted maybe 20 days...
No way they would have lasted over 20 years with those tactics. Outlaw gangs were small and traveled light; a few men on horseback with only the things they could carry. When they wanted women, they would rent them from a bordello. Some outlaws did have families, like Jesse James, but those guys basically had secret identities and nobody knew of their outlaw lives.
Dutch's gang was more like some gypsy caravan than an outlaw gang. They wouldn't have lasted more than a couple of weeks with that huge entourage.