Putting together a 5 bottle dream team:

Strannahan's - because you're from CO
Middleton Irish Whiskey (I didn't see a price range, so why not)
Johnnie Walker Blue - yes, its a blend, but nothing under 35 years old
Jack Daniels Single Barrel - if you feel you need an american classic
McCallan - 16 yr or higher

Cigars - for a reasonable price
Nubs - Great smokes, last forever (about an hour) look great in photos
CAOs - anything in the Mx2 variety is smooth as anything I've ever smoked

I don't always indulge my vices, but when I do, I spend all of my money on them.