First, I had three characters so far. A mage (totally blew because I expected way more spells back then), a warrior/monk with restoration and a thief/assassin with archery. That let me finish all questlines, and invest in most skills with one character or another. I made extensive use of Destruction, Alteration, Restoration, Conjuration, Illusion, Enchanting, Smithing, Two-Handed, One-Handed, Heavy Armor, Archery, Sneak and Light Armor. The perks in Pickpocket, Lockpicking and Speech don't hold up to the other skills in my opinion, which basically leaves me with Alchemy. Sadly, that's not enough to shape a character, and I can't see another combat option I'd like to try - except blocking maybe. But that would force me into One-Handed again ...
Besides the loss of spears, throwing weapons and crossbow from Morrowind, the few spells we have left in Skyrim really makes it hard for me to replay this game with another character. The perk system was supposed to force us into choices, so we couldn't do everything with one character, but I just don't feel it. None of my characters are at max level, and could still easily change their whole playstyle.
Second, Radiant Story is designed for people that only play once. The game directs you into regions you haven't been yet with that specific character, so you get to see as much as possible. While basically a nice idea, this ultimately results in the same experience with every character you make. It's very hard to say "The Reach looks nice, I will save that hold for my Orc character" when the game constantly pushes you into that region.
I put 230 hours into Skyrim so far with several characters, and I have the feeling I ... completed the game. I even did a lot of things several times - I lost count how often I cleared Bleak Falls Barrow, Korvanjund and Shearpoint.
I am now off to play with the character generator once again. Maybe the beast races will inspire me to try something else. Play a totally non-combat thieving Khajiit or something ... :sadvaultboy: