It depends on one's outlook. I know people who's attitude is both "boy that was a dumb tattoo to get at 18" and "dumb 18 year old me is still me, and I don't want to remove that tattoo any more that I want to remove that part of myself".
Obviously circumstances may change if the tattoo is offensive.
Your second perspective captures my personal take. I feel indifferent about the actual ink at this point. It’s more about a personal/symbolic mark of who I am, who I was, maybe who I’ll be - all the same person. No regrets.
Obviously circumstances may change if the tattoo is offensive.