No but I always expect it eventually will, and look at everything I put in my checked luggage as if I saw it for the last time.

Yes. Up to 1,131 XDR per the 1999 Montreal Convention; or up to 17 XDR/kg per the 1929 Warsaw Convention. What have I won?

Just for the record: luggage is usually not lost "when flying" but when moving through the airports, although the former would admittedly be much more dramatic.