The debate between new and used is usually fairly cut and dry when you talk to people - buy new and pay more or buy used and pay less. Its accepted that used will have a certain amount of wear on it and not come with all the perks a new item would normally have, but overall that's the price you pay for not paying full price.
Over the years I've gotten to know and be acquaintances, if not friends with, a fair number of content creators. Artists, writers, musicians who make their living (or supplement it) through books, games, and music sales. I'm a fan of a fair number of companies that do business with selling software and services, some of which have seen ups and downs. On top of all that I've got a liking for some of my local stores and businesses.
Because of all this, its put a different twist on how I'm seeing the new versus used debate, and has me leaning more towards buying new. Not because I'm rich, mind you! To be honest, for a while I felt like it was kind of silly to buy new - you're paying more for, what? On some things, like books, DVD's and games, there's a good, compelling reason to buy used! Especially games when the store you go to provides a better return policy and 10-20% off the price of new when you buy used. Arguably, its stupid to buy new (at least with them).
When I buy a product new I'm generally buying locally. This is a wonderful thing since, well, living on an island means money generally has a harder time getting here than leaving here. I might not be getting the best price (shopping at Amazon or some other online retailer might save me, sometimes even after shipping), but at least some of the money stays here, and usually paying someone's check. I like this, especially since my own work depends on other businesses doing well. Do I order online? Yes, I do. But generally its for things I can't get here. Maui, not being Oahu, this issue can come up a little more often than I'd like.
The other trick with buying something new is I'm supporting the people that produce it. I've liked enough small, niche companies or topics over the years (SNK being a long time favorite) to sort of dispell that "all companies are greedy, evil, and greedily evil" misconception. Yes, companies are for-profit, obviously, but that doesn't mean they're swimming in cash. Likewise, if they're not making money doing something either they'll go out of business or stop doing that thing, whatever it was. I've seen companies I've liked go out of business, undergo layoffs, and even get bought out then gutted or changed to the point where they're not really the same company anymore. So, supporting products I like and the company that makes them has gotten a bit more important to me.
To make things one step deeper, I now know people who are involved in those products. I've been fortunate enough to have conversations (and play online once) with a staffer at Arena.Net, the maker of Guild Wars. One friend of mine writes and publishes role-playing games, whereas another is a writer, whose works can be found not only in her own novels but also anthologies. A good, long-time friend of mine is an illustrator, having done work for a fair number of books (and at least one video game!), plus another has done art for video games, movies, television shows and lord knows what else. I've known more than bands from my college years - folks I went to school with - going to their concerts, buying their self-published CDs and other merchandise. I've even, through a friend, got to meet a gentleman who works at Microsoft and had his hand in the 360 and the Zune (two products I own and enjoy) - even got to play a DVD trivia game with him and his family (Shout It Out or something like that). This has sort of humanized the whole process - its gotten a lot easier for me to see the people behind the products, you know? When I buy new, it benefits them.
I'm very happy its getting easier to buy things digitally now - its getting easier, cheaper and more convenient, plus with at least Borders I'll be able to buy digitally, locally, as well.
I'll be honest - sometimes I really don't want to swallow the price of buying new. Sales happen and coupons come around. Sometimes I will go ahead and buy used. But I have to say - I certainly don't feel like it is stupid to buy new. Now, I don't feel greedy or selfish for buying used - but I'm leaning a bit more the other way.