For me it depends on availability. If its stocked by YLCB I'll empty it and get another the next day. If I got it somewhere else, like Alberta, BC, Alaska or (gasp) Newfoundland, I'm a little more careful.
The Yukon has started stocking some really good stuff on a trial basis, and I'm doing my best to make sure its worth their while.
I was in Ireland in 2010 and brought back some old Bushwhackers. And that's when I decided I liked rum better. Now I've got about 40 different rums, enough that my family gave me a re-purposed TV cabinet that happened to match an antique china cabinet that my wife inherited.
I guess my main problem is that I have trouble making decisions. So, faced with a choice of forty, I empty Old Sam, Goslings and Screech with disturbing frequency.
Tonight I just happen to have emptied a Havana Club 7yo.
Postscript: last night I emptied a Matusalem. Tomorrow I might crack one of my Diplomaticos.
Oh Jeez! Another decision.
Never pass a bar with your name on it.