I tend to buy when I have the funds, which lately is every other month or so. Because of that I tend to get bundles of budget sticks to hold me over and pick up a few nicer ones here and there.

So my assortment looks something like this, but never all at the same time.
Boxes / Bundles:
Schizo
Casa de Garcia Maduro
Sancho Panza Double Maduro
Nica Libre

5 packs:
Undercrown Corona Viva
Brickhouse Maduro
Room 101 Big Payback
Diesel UHC

Singles:
Anejo 46
Anything that looks good on a B&M trip
Bomb and pass sticks that have not become 5 pack purchases yet.

This group of Bums, and the poof site group before it, really helped expand my cigar lists beyond the junk my local B&Ms recommended for a newbie.

I see my box list getting substantially larger once I make the move to sample other cigars. Good thing I have some storage space lined up as I only smoke a few a week.