I might spend about $300 a year on this hobby.
Usually between November and January I'll buy a few boxes of some midrange smokes that I enjoy (Devils Weed, Iguana, Erin Go Bragh for instance) and I'll spend about $100 on just sticks that are higher dollar.
Gives me a chance to sample some really nice cigars.
I doubt I'll ever have the money to get a box of the Ashton Heritage (one of my favorites) for instance, But I readily acknowledge that I'd rather have 60 of my mid range smokes to enjoy all year than 20 smokes that I'll constantly be asking myself
"If I smoke this when will I be able to afford to replace it?"
So I buy the expensive sticks when I can and hoard them like a miser