I've only ever had two characters, and I left the first one after taking a 3 month hiatus from Skyrim.

I just went through 5 characters... in 2 days... argh! I need to pick and stick with it

The early game is really the best part, before balance gets entirely out of whack. By level 40 things were completely out of hand, so that's about as far as I have gotten.

I save a lot so if I don't like an out come or change my mind I can go back and change it.

I tend to play a main then have a few other characters that each are unique so they play different and look / wear different.

My main is a Breton mage turn nightblade who uses bound dagger and bound bow with mage armor (alteration) & conjuration. Very high magicka

My second is a Nordic (Teutonic) knight in full ebony with 2h. Very high stamina

My third is an Imperial spellsword with 1h, block & restoration. also uses destruction (often I go 1h & destruction). wears light armor (dragonscale with a hood - Combining the look of the Imperial Dragonscale armor from Morrowind crossed with the look of an Imperial Crusader in Oblivion ).

My forth is a Dunmer Battlemage with dual destruction & heavy armor (hardened falmer or daedric).

i have started innumerable characters, but ive actually put a little bit of time into about 7-8. i have almost 1000 hours played between them, the highest level is 61 warrior with 145 hrs and my current character is a lvl 59 mage with around 100 hrs. the crazy thing is, im still discovering new things and finding new quests to complete especially in the DLC

When i think it′s time for my character to settle down i just or Retire them or just lead them home and remove all quests i was doing and put them resting there, then i start a new one