This bothered me especially in New Vegas, where it seemed like the majority of the world was "Primm Resident" or "Goodsprings Settler". At least Skyrim doesn't go to that extreme.

I never understood the fascination with respawning dungeons. Why would I want to continue to clear out the same dungeons over and over again? Quest objectives would be the one thing I could agree on. The only exception was that one in Oblivion where the marauders were attacking the bandit encampments. I went through that one a couple of times, just to watch the fights from a distance. I don't think the bandits ever came close to winning a single fight...

If I could actually use the cnstruction set without it crashing on me, I planned a unique guards mod, so that almost every guard and soldier had their own families, backgrounds, and time off... Purely in terms of life rather than immersion. It doesn't bother me a huge amount, since you don't know everyone's name, and with extremely violent/dangerous people, probably never will.

Agreed, it feels kinda pointless. It's not like the amount of bandits, outlaws and hostile warlocks in any way a decreased despite the PC's efforts. So in the end, I might just as well leave the original bandits be. Especially after a while, when my character has reached the point when money isn't an issue any more and he/she isn't interested in the loot.

I have to agree with the OP, it was a mistake to bring that over from Fallout 3. You can't really introduce depth to somebody named Prisoner.

Indeed. I personally never go to a dungeon I cleared out unless another quest takes me there.