I think most players are gonna at least check all the boxes to make sure they don't miss anything important, because if you're experienced with CRPGs
They could make them account-wide. If you dont get all from your first play-through, get them from second one. I generally hate design what forces player to do something, like in DOS2, there was billion places to loot and check.
I like the idea of replaying the game. Sure theres enough depth/stuff to play it again. Play the game, take what you want, if it feels you wanna go for another play-through, you get the rest. Thats why I would sell another Character Pack, btw. They could add somekind of vision-mode, for all lootables. Or Detect Item spell?
