So when you do guys start another character after your first one? Do you wait til your level 50+ before creating another one?
Or you just create another one right after you've gone up just a few levels -- a completely race just to compare it side by side with the first character you had?
Or only when you've finished the main quest with your first character?

Basically, when's a good time to start a new character?

When you get bored of your current one.

In both Oblivion and Skyrim, I was about 20 hours in when I made a new one.

Mainly to see a different play style, or just to create a new face (I like the char gen).

However, In oblivion I think I only had 7 characters total across PC and 360, so I'm not exactly a serial character maker!

I play a variety of different characters each with different races and builds just to see what I like. I'm just now settling on an archer/thief/assassin type. I've deleted all my saved games and am now going to start this guy right now (after this post). Then I'll play him till I get bored, and switch to a different style and run a different route. After that I'll go back to the one I want to play as.

I made 2 characters got them both to level 25 and deleted them both. It seems I always find a flaw in their design. but soon I'm probably gonna start a Paladin build and keep him until I finish the main quest at least I hope so.

Eh, I create new characters almost right away. I'm juggling four right now, each with a different play style. I've got my pure mage, heavy combat, light combat and archer.

when they reach a natural conclusion, usually after 1 guild.

I typically finish the main quest with my first character after running him or her to the level cap and assessing my perk and skill picks, and then retire that character. I then use the information so gleaned to design subsequent ones. I will also start a new character if an expansion or DLC alters a fundamental aspect of the game; such alterations usually mean I have to alter my builds, which is something I can only do with a new character*.




*There are console commands I could use to do it, since I'm on a PC, however using them for a full rebuild tends to not be wise as doing so can permanently glitch the character.

Just like those early stones you get to choose I rotate between the 3 main builds..Warrior, Thief and Mage

To keep the "experience" unique I pick guilds that fit their class. Mage = College of Magic, Thief = Dark Brotherhood & Thieves guild, etc. Also the Thief picks all the negative "What's in it for me" answers during conversations.

Also I noticed each companion / follower have unique skills. Lydia for one cannot pick locs so if I am playing my Mage and wish to maintain his playstyle I bring Aela along for the ride since she can pick locks instead of my mage having too