Tempted to restart S'hawn on Skyrim...

There are a few side quests that I missed and need to go get. For example the beggar in Ivarstead (Do his quest, THEN assassinate), kill the pirate captain for the executioner in Solitude (I WANT THAT AXE!)... and the one enchantment I want to get: Poison Resist. Planning on fusing it with Disease Immunity in order to make... The Amulet of Purity!

On the other hand... the original S'hawn is very close to me... I've been through a lot with him... but can I do everything S'hawn's done all over again? Do I really WANT to?

Choices, choices...