Sacrosanct
Legend
See, I don't even try and do that. Different editions are different systems; trying to recreate a 2e character in 5e is like trying to port my World of Warcraft characters to D&D. Maybe you can do a loose adaptation, but it's like those movies that tag themselves as "inspired by a true story". A whole lot of changes got made in between the two.
Those characters had their stories, their time on stage came and went, best to move on.
I think it really depends. I was able to port my halfling fighter/thief from 1e into 5e near flawlessly. Made him a straight fighter with the urchin background and skulker and dungeon delver feats. Felt almost the exact same in game play.