Quote Originally Posted by Mirage View Post
I think it would be fair to let people take usernames of characters whose content IDs haven't been active in several years.
This is actually what Blizzard does with WoW. If you transfer your character and the name is taken you can put in a request to get your old name back. If the "taken" name has been inactive for over, I believe, 6 months they will instead give the name to you.

A few of my friends have done that in the past.

I would definitely say that's probably the best option.