1. Oldest possession: Either a bit ~2000 year old Roman glass from Jerusalem, or ~2000 year old potsherd from somewhere in Israel. I'm not sure which one is actually older.
2. Posession owned longest: Leo the Cross-Eyed Lion, a stuffed lion I was given when I was only a few weeks old. Leo's from a leavings bin; his face was sewed on wrong, so it's lopsided and he's cross-eyed, but he slept with me for years.
3. Most expensive: Skuld, my 2002 New Beetle. I imagine a horse farm could well surpass that eventually. :)
4. Most precious (to me): Hrm. There are about three possibilities which means a great deal to me, but I'll have to go with BlueJeans Elephant. BlueJeans, or BJ for short, is an elephant I was given when I was four. He was made by my paternal grandmother (not the one who passed away this year), out of my grandfather's favorite pair of blue denim jeans. BJ has this surprisingly comforting aura to him; anyone who holds him feels better, and he's nursed several past roommates through horrible flus. He's been mended rather clumsily by an 11-year-old with thread and needle, but he still has the place of honor on the table beside my bed. And always will.
5. Rarest: That'd be another hard one. My grandfather's set of Pogo books? The set of first-edition Oz books from my grandmother?
6. Oddest, strangest, or silliest: Handmade, button-eyed, bat-winged cyan Plushie Cthulhu.
7. Newest (non-food): plushie horse named Amigo, in honor of the recently-deceased horse of the same name at the stables, who plushie-Amigo somewhat resembles.
8. Which possession most sums up my personality: I have... no idea, at all.