I retired my Brute (fighter/tank, in as much as tanking works in Gloomhaven) in Gloomhaven, and brought in his replacement. Because we already had our tinker/healer replaced with another warrior, the brute's replacement Craig Hart, a genderless idiot rock person who can use the power of earth/leaf to heal sometimes, but is considered a failure among rock people because Craig apparently can't control any elements. Craig also throw rocks at stuff, causing splash damage (which ignores armor), and has the old PC attacks we're aware of that ignore the normal "you can't harm allies" rule, and only one enemy we've seen can do it.
The win was I was able to hold back enough to keep to exactly 7 xp gained (my in-mission goal was 7 or fewer xp, which gives double the credit of a normal goal, with a character who can earn 20 fairly easily), and weaken but not kill enemies to let our Scoundrel kill all 15 vermilings in one mission that she needed to retire as well. Also, I got to use the phrase "Hulk Craig is strongest there is!"
Craig's retirement goal is to become a hero and defeat 4 boss monsters (we have seen 1 so far), because they saw a cloud and thought it was a dragon. I'm not sure why seeing a cloud or a dragon makes you want to be a hero, or why killing 4 boss monsters is the exact way to be a hero, but Craig is dumb as hell.
The now-retired Scoundrel will become a Diviner, a class which does not normally attack enemies, which will be wild.
In conclusion, Gloomhaven is a great game if you put a nonzero amount of effort into roleplaying.