Some kind of partial identification would be necessary... Maybe like this? a) it's a weapon, and it's a sword or a polearm (ahem, I'm not going there!

) or whatever, b) it's armor, gloves, or helm, etc, c) a wand, d) a Red Book (e.g. a junkart), or whatever....
Re: the wandering salesman, I was thinking of a fantastic (imho) and very,
very twisted series of games called Exile. (reference:
http://www.spiderwebsoftware.com, and no, I don't work for them. Just look out for the cute spiders and the slappy monks, is all I have to say!) Among many other things, at least one those games does have a travelling salesman (I forget his name) who pops up from time to time, and for that matter there are caravan routes as well. The routes work somewhat like a quest, where you have to deliver a cargo, intact, within a certain time limit...and sometimes you don't know where the destination is located yet!
That game does have a certain amount of randomness but is underlain with fixed quests, as well, though you play a group of characters rather than just the one.
Before someone jumps on me, I certainly
don't want ToME or any other Roguelike to become an echo of Exile, but there are some good features in that game that would make perfect sense in a Tolkien-themed world, once properly adapted.
Anyway.... FWIW.