This is probably my favorite thread I've read since finding this site. Pouring different whiskies together is just a great way to "play" with our playthings!
I have two strategies:
First, I have a biggish decanter (1L?). Into it goes a generous pour from every non-special bottle I get my hands on. Into it goes the last little bit of (most) bottles that I want to prevent from oxidizing. Into it goes anything that I don't especially enjoy. This decanter provides a few benefits:
* I get to use the decanter, which I received as a gift.
* I have a bottle that keeps changing.
* I don't risk the last bits of a bottle.
* I get some use of the disappointing bottles.
* I have a ready supply of juice I can pour with zero regret over losing a measure of something I care about.
* I get to "hold onto" all my old whiskies that I might not ever buy again. Forever, that decanter will include at least a little bit of those oldies for my sentimental heart.
Second, I have a smaller bottle (20cL?) that previously held Lagavulin 16. Into it goes a measured pour of each of my good bottles. (I'm not a real high roller; "good bottles" for me are things like Laph CS, Springbank 100 proof, Glen Scotia 12, Laddie Rocks, Talisker DE. Stuff in the $40-$60 range.)
* This bottle is more of an experiment than anything else, but it also effectively provides me a new & different high-quality whisky without me shelling out for another one. It's tasty.
* Like the dump decanter, it preserves for all time a small piece of the good bottles that I might never buy again -- as long as I never completely drain it.
~ Ol' Jas