I find it easier to just respec a character. I had a Sorc healer but then I lost the overload bar and then I felt like there was nothing interesting to playing sorc healer, just using resto-staff skills.
So I swapped them to pet sorc and made a Nerco healer when the new class came out.
I retire characters when I need a slot available to level something new. I leveled plenty of toons but in reality only ever really play one for end game, 1 for crafting and a couple for inventory space.
I retired my necromancer (that was going to be my main, it was the first class I was genuinely excited for) after it was nerfed into the ground after Elsweyr launched and I found the siphon ability to just be too buggy. Didn't delete it, but I basically treat my character selection screen as an ordered list of highest to lowest probability / frequency of being played. Been maining a magsorc since and been fairly happy, so that's been my main.
I played alts a lot more in ps4 but now I pc a fable with a couple alts but nothing much I have a move hate relationship with my Magdk I’ve tried to retire him but no other class is fun to me all Stan classes are boring hate all the spammable
DC PC NA
Magdk - main
Stamcro - alt
AD PS4 NA -retired (PC runs way better to play on console)
magdk
magblade
stamplar
magden
magsorc
I make alts all the time and usually kill them off when the leveling gets harder. I one Templar, my main who is maxed out on everything done all the content and achieved all that is interesting to me. Its too easy.
I never retire my characters. I do try to leave them in a nice place while I am ignoring them.
Yes, I almost always "go back to Rawl'ka" before logging out with anyone.
Tenesi Faryon of Telvanni - Dunmer Sorceress who deliberately sought sacrifice into Cold Harbor to rescue her beloved.
Hisa Ni Caemaire - Altmer Sorceress, member of the Order Draconis and Adept of the House of Dibella.
Broken Branch Toothmaul - goblin (for my goblin characters, I use either orsimer or bosmer templates) Templar, member of the Order Draconis and persistently unskilled pickpocket
Mol gro Durga - Orsimer Socerer/Battlemage who died the first time when the Nibenay Valley chapterhouse of the Order Draconis was destroyed, then went back to Cold Harbor to rescue his second/partner who was still captive. He overestimated his resistance to the hopelessness of Oblivion, about to give up, and looked up to see the golden glow of atherius surrounding a beautiful young woman who extended her hand to him and said "I can help you". He carried Fianna Kingsley out of Cold Harbor on his shoulder. He carried Alvard Stower under one arm. He also irritated the Prophet who had intended the portal for only Mol and Lyris.
***
Order Draconis - well c'mon there has to be some explanation for all those dragon tattoos.
House of Dibella - If you have ever seen or read "Memoirs of a Geisha" that's just the beginning...
Nibenay Valley Chapterhouse - Where now stands only desolate ground and a dolmen there once was a thriving community supporting one of the major chapterhouses of the Order Draconis