I'm always more on how cool an artifact is, not just how useful (though in some cases usefulness enhances coolness, such as a weapon or armor). For example I had one dwarf in a mood make a wooden figurine, effectively useless as it cannot be used or placed, just sit in a stockpile somewhere or sell for far more then I can buy back from a caravan (plus I have plenty of stuff to trade anyways).
However, it is a figurine of the dwarf named after me laughing as a dark strangler begs for its life as well as an image of my dwarf being promoted to militia captain. Just awesome (IMO), far better then an iron sword of the highest quality with spikes of iron and whatever (though my coolest one was a silver spear studded with iron and other things that had an image of the diety of murder, or something like that, on it).
As for 'win'? I once had a named dwarf (as in, a dwarf I give a unique custom name to) lose both of his arms in a fight (one at the elbow, one at the shoulder), survive (this was in mid 31's, so infection and such was in, and medical science was.. Limited..) to the point of recovering completely (just wandered around a lot) and then fought off an attack of a giant cave rat when the caverns vomited up a bunch of monsters into my fort.
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