tough one, one of my most emotionally valuable items is a Ruger MKII Pistol that was owned by my grandpa. Theres not an item in my current possession that I cherish more than that.
Other really notable stuff would be my collection of Signed McFarlane NHL figures. I've got a few spanning from Yzerman to Ovechkin.
As far as money is concerned though I've got a binder full of nhl rookie cards that include the likes of Patrick Roy, Bobby Orr, Phil Esposito, Steve Yzerman, Mike Modano, and tons of other Hall of Fame and current players. Theres no telling how much I could get for them if I were to put them up for sale.