Interesting in my travels on my second character. Last time I'd run into all kinds of odd stuff like Old Orc, random people asking me for help and whatnot but when I'm out and about I never see anyone. Poor me. Anyone know if this is in-fact a true bug or intended? Or am I just unlucky?

bump

I doubt it. If that is actually the case, it's a bug-- no way that's working as intended.

Perhaps do a bit more traveling about?

Also, this just occurred to me, but perhaps what you're thinking of was actually a quest and not a random encounter? Some of Skyrim's quests are much more dynamic-- ie, instead of just meeting someone in town who needs something, sometimes you'll find someone by a cave who needs help clearing it. Maybe it's one of those?