Yeah, no kidding. Most of Bukowski's early books sold for a dollar when they were new:
Flower, Fist and Bestial Wail, $1 Longshot Pomes for Broke Players, $1 Run with the Hunted, $1 Cold Dogs in the Courtyard, $1.25 Confessions of a Man Insane Enough to Live with Beasts, $1 All The Assholes In The World and Mine, $1
Then came John Martin, who put out the set of five broadsides for $10 each. Which must have seemed completely insane and unbelievable to the people who bought Bukowski's work at the time. But he was selling rarity, as the broadsides were only editions of 30. When he put out At Terror Street and Agony Way it sold for only $4.
In the same issue of The Outsider are Jon Webb's pleas for people to send him $2 to pre-order It Catches My Heart In Its Hands. After publication it was meant to sell for a whopping $5 autographed and $3 with no autograph. But all copies were autographed, so I guess if you sent Webb two bucks in '62 for It Catches, you made out pretty well. ;)
One I could have bought new was ME AND YOUR SOMETIMES LOVE POEMS, which Bukowski co-authored with Linda King. I think it was a buck. I was a poor student and either didn't have a dollar on me or in some lame-brained way was being too frugal to buy it. Years later, I did buy a reprint from Linda and she wrote a nice long inscription and signed it, which kind of makes up for not having grabbed that first edition. I'm not really a collector, but I always loved the title and concept of that book, and felt dumb for missing the opportunity. The text is the main thing for me, but some rare editions have an aura to them, and for me, this is one of them.