If you do the same things with your characters, then yes. Personally, my first playthrough was as a fighter/thief/assassin. That's 3 guilds, plus the two main quests (sided with the Stormcloaks). My second playthrough was as an orc fighter/mage. 2 guilds, same two mains, 1 of the guilds "new". Sided with the imperials AFTER finishing the main MQ. Dossiers offer interesting implications (total subcontext, never alluded to by the NPCs AT ALL) IF you read them. Offered a fresh playthrough experience, especially considering that I RP the PCs. My third, I'm just cleaning up the main MQ now with a "pure" mage High Elf who, of course, thinks his s doesn't stink. Being that he thinks he's better than everyone else, including the Thalmor, he dabbles here and there just to say, "See, I can demolish you on your own terms, you pitiful fool." He'll kill just about anyone "just because". Anyway, he didn't side on the civil war yet at all and lo an behold, when it comes time to confront Alduin, after 100s of hours of play, I experience something COMPLETELY new (and very cool) as a condition of "getting where I have to go" (avoiding spoilers). Since MOST players will probably have sided one way or the other (on a single play through) before this point, it's something many will never experience. ANYWAY, point is, if you follow the same paths on subsequent playthroughs of the same world, why would you expect them to change? RP a different character and the experience is different enough to make it feel (semi)new.
I'm playing with a Thief, a Tank/Battlemage and a Conjurer. i'm not talking about feeling with the same character. i'm talking about more random things. Not find anything new the game it's the same as hearing the same dialogue from the same Guard:
"You know what's wrong with Skyrim these days? Everyone is obsessed with Death"
"You know what's wrong with Skyrim these days? Everyone is obsessed with Death"
"You know what's wrong with Skyrim these days? Everyone is obsessed with Death"
Just C'mon.... The same dialogue 100x times. I stabbed that guy.
Edit:
I have had bandit raids on dawnstar and have seen bandit hunting parties hunting mammoths and attacking giants, I have seen vampires take on towns and massive amounts of spiders going after townsfolk, the problem is, you are probably fast travelling everywhere.
Saw that alot also. But you see that too frequently. One thing i saw, and i will never be able too see again. Was a Charus killing some Horkers next to Morthal. It was an amazing sight.