The other day in a conversation elsewhere, I asserted: If you have a choice between bootlegging something and buying it used for a reasonable price, buy it used. There may be benefits that you don't immediately see.
Buying a used copy of something removes it from the general pool of available copies. That creates, in the long run, an incentive for the item to be reissued. If it's that much harder to find in any form, it becomes that much more desirable overall.
Buying a used copy puts money back in the hands of a merchant who can then bring that many more things to other people, you included.
Buying a used copy puts money back in the hands of an individual who can then buy that much more product, new or used, and further stimulate the general market for such things — of which you're a customer.
Now, to draw a distinction or three. I know some folks who are fans of things that are really hard to find in any form, and have resorted to bootlegging to get those things. Am I going to consign their soul to the lower planes for that? No, it's just not something I feel I can opt for myself.
I suspect at least part of this attitude comes from me having modulated my intake of a lot of things, and finding better ways to (legally) satisfy my interest in them. There's NetFlix for movies, Just The Disc and other such stores for music ... but underneath all that, there's also the understanding on my part that behavior which amounts to hoarding is not good for you. (It's something I've touched on before.)
I don't believe for a moment that my behavior is going to have any effect on the net consumption behaviors of the vast majority of people out there, who are rapidly growing accustomed to getting everything for free (free to them, that is). But that doesn't mean I'm obliged to follow their example, and kneel at the same trough.