You would loose less gold buying things back with a high reputation and/or barter.
The homestead chests (available the portal after the Hall of Heroes) can be moved to a more convenient location (near a handy waypoint). Once unlocked, there will be a 'send to homestead' option in the right click (or whatever the controller button is) context menu in the inventory. For other chests, I'd probably avoid the evidence chests from the legion headquarters building, in case that causes issues if a character gets arrested as some point for stealing or vandalism.
Some AI can pick up items left directly on the ground (ie opponents picking up and using dropped potions), but I'm not sure if that is the case for any friendly NPCs around town.
