Im still on my first char but am wondering when to retire him and move onto another. I am rp'ing and have set goals as to what my char wants to achieve (ie defeat the stormcloaks) so i guess i'll stop with him after he completes his goals and start again with a new character and do something different depending on their personality, history and motives.

So when do you decide you've had enough of a character? do you have set goals or do you complete every quest and join every faction you can with one character?

I usually join the factions that fits more with my current build and complete it, then I do some random quests like the dawnstar or malkhart ones, then I finish the main quest and finally I join a side in the civil war, after that I usually retire the char but keep the save of course, just in case I want to do something else with those chars

I don't retire mine, it's not that formal. Usually either I run into a bug that ruins them and I have to start over or I just get bored and make a new one.

Basically, when I complete what I set out to do in the beginning. I have one character who only made it to 63 hours because she finished what she set out to do. I have another who made it to 176 hours and could've gone longer, but didn't fit into the rp.

I have kept my original character since 11-11-11. Of course, I've built several and have "retired" several, but I still have the original Dunmer and am trying to work around some of the leveling/perk errors I made with him because I didn't know what I was doing at the time.

I only connect with one character and I never retire her.
To all intents and purposes she exists as an entity in a world, she's not a "thing" that I can retire when I get bored of her or when I think she has achieved "everything".

Thats a very interesting take on it which i havent heard before.

Doesn't it get boring having 100 skill in EVERYTHING that you use, or having done everything?

I can't stand having an archmage, companion's leader, Dark Brotherhood saviour-assassain, godly thief leader, Imperial commander Dragonborn guy, who is level 81 and can walk through anything.

When I create a new char I set a goal for him and unless something different happens during his playthrough I retire him as soon as I achieve that goal.

Nope.
Also - uncapper
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But we have a way to go before Niamh gets to that point.
Also - as I said, it's not me that gets there, it's her - so if she is that good then, well, that's how good she is.
AND - she is not the Dragonborn, so none of that counts.

In Skyrim I retire them around level 30, regardless how far in the questlines they went. Level 30+ seems too overpowered for my liking.

Ask me after I have done the main quest or completed a faction. Only 400 hours in, no sense in rushing things now, is there?

After I feel the need to create a new one. And I usually don't completely "retire" them, (unless my save game bugs out and refuses to start...) I just pause the playthrough so I don't get bored, and try out something else for a while.

When I get bored I guess, but it didn't happen to me yet, both my start characters are up and running.

I retire my character after I ...

When I create one, I choose which guilds they will join, and any other types of quests I want them to finish, then last I will do the MQ (and not with every character), then I am ready to retire them and wait to see if I need them when DLC comes out. I only have one retired. My original mage at level 45. Of course, with THIS game, I am hesitant to ever use her again because I know how glitchy all her saves are.

when i play dead is dead and a mammoth lands on his head

Usually after finishing the main quest (which I may or may not start before finishing other goals) I retire my characters. Or until I get bored and feel like having another playstyle. Whichever comes first.

I make characters in order to tell stories to myself. When I feel my character's story has come to an end I retire that character and start another.

damm lol no, no rush

Whenever I've done everything there possibly is to do. I've done that on just one character so far. >;

When the game becomes unstable! Really...

I'm a little like PhonAntiPhon. The time invested on a first character is unique. Sadly mine is in the garbage heap now thanks to bugs.... I would keep the same character forever if I could. ( on xBox)

When I get bored, have nothing to do, or simply figure out how to make better/more interesting character.

It's a bit vague.... I stop playing a character whenever it feels "done". I certainly don't try to go for 100% completion on any of them.

(My first character lasted ~90 hours; had only done the Companions guild, and hadn't visited 2 or 3 of the cities marked on the map. It was a light armor, sword&board warrior/rogue, and finally got around to finishing the MQ and Civil War when she was in the low 50's. The next character is still in progress, and is a heavy armor, 2-h axe warrior. Also, a chance to test out one of the replacement bodies and several armor sets. The one after may be a mage.)

I've never really defined personalities for my characters. Instead I define them by the playstyle/skills I'll pursue, and the set of mods I'll use.

At some point I suddenly decide that the current character is too powerful for the petty sidequests he's given, especially if he's already done the main quest. Since Bethesda makes everything accessible to every character, I save some quests and guilds for other characters so there's always something new to experience when the feeling of deja vu is growing strong. For example in Oblivion I never finished the fighters guild, I saved it for a character that has never come...