OK, first the rant:
Bethesda, if there's just one thing you should have brought over from the Elder Scrolls games, it's being able to see categories for Weapons, Apparel, Misc, etc when trading and transferring to containers. Gaarrrrghhhh!
It's a great game, but it can be a bit of a chore at time.
So how are other people handling this?
I guess the big question: Are regular storage containers (non-workbench) in settlements safe? So if I put all my Armour in one place, Guns in another, etc, can I be sure it'll be there when I return? That seems to help, but I'm being cautious about it, and not leaving anything too good outside of the workbenches.
I never played as much of a looter before, but I just can't help it this time round.