Loss on rebuy is a subjective thing. I am almost always carrying quite a bit of explo data for example, it's a handy way to quickly apply fairly precise amounts of influence to a faction that controls a dockable asset. On the rare occasions I get popped it
matters to me, and it stops me being too complacent.
Right now I have 22 pages of explo data on me, and while I could just sell it whenever I dock on my carrier... well where's the fun in that? When I eventually get back to the bubble I can do a lot more with that data than just earn cash & get tags, assuming I manage to sell it