Paring down with what's currently on hand:
1. Beretta 391 26". I'd have to think long and hard to decide 12 or 20 though as I don't hunt waterfowl.
2. 77/22Mag SS Boat Paddle w/NF 3-10x42 SHV/IHR
3. Kimber Montana 270Win w/1:8 Lilja @ 22" and 2.5-10x42 NXS w/IHR reticle
Non of the above have much "sentimental" value as I don't think I've owned/shot any of them for more than 10-12yrs. That said, if I'm having to choose 1 of each going forward then the above 3 get the nod because they're simply trouble free and most likely to stay that way a good long while.