I typed out my eight characters, by Name, Race, Gender, Class, Level, and Factions (Active status or Completed).
I've decided that five of them are absolutely worth keeping around. The other three are...eh. I'm thinking of deleting them entirely. I love Skyrim, and can easily play it until the next TES game. So there's always opportunities to revisit and re-roll the ideas/intentions behind these three.
The three I'm considering for deletion are:
1. Gi'Anna, Female Khajiit Fighter, Level 33, Harbinger of Companions, Main Quest Active.
She was my first character, and as such I made a mess out of her Skills and Perks. Compared to my Level 36 Nord Fighter, she's just not viable. He does it better, has started the Companions, and is also Active in the Main Quest.
2. Maylissa, Female Imperial Cleric, Level 16, Dawnguard.
I uninstalled DG because of my frustration with random vampire attacks. More specifically because it affects EVERY character file. It was fine for her file, because she was created specifically for DG as a vampire (and all Undead) hunter. She hasn't been played since I uninstalled DG, and I'm STILL undecided on reinstalling it.

3. Skeeme, Male Argonian Assassin, Level 17, Dark Brotherhood (Active).
I created this "Argonian scum" for fanfic. I thought I'd try my hand at him as a character, and he just feels so...flat. I love the DB questline and its members so far, but this guy just doesn't feel right for it. I'm thinking a re-roll is in order since I definitely want to play through the DB.
Am I nutty, or does anyone else evaluate their characters this way? I've read that some people re-roll characters dozens of times.

Sorry to rant and rave, but I like to discuss this kind of stuff.