I've never bought a box

I bought my first box about a year into the hobby. I got a job at a cigar shop and about a year after I started, we had a Perdomo event with Nick Perdomo himself there. I really liked the new (at that point) Lot 23's so I bought a box and had Nick Perdomo sign it. It was pretty cool.

As far as when should you buy a box? I have to agree with the answer: When there is a cigar you want 20 of.