If that was true, Jack would make 10,000 of them, not 300. Then they couldn't be resold for a profit.Jack wouldn't want someone paying more than the $5.00 original value!
He knows full well this stuff will end up on eBay, and if it sells for some ridiculous amount, people will talk about it. They'll talk about his record company. It's marketing. You can wrap it up in a wacky gosh-aren't-we-counterculture package, but it's really nothing but marketing. That's all any limited edition anything is. You are giving something a value that it wouldn't normally have by making it scarce.
There's nothing wrong with that. But it shouldn't surprise you.