It's a very short-sighted mindset.
For instance, I never would have purchased Portal brand new (via the Orange Box on the 360). But several people recommend that I pick it up, so when it dropped to 10 bucks or so used, I grabbed it. Fell in love with the game. Stayed up all night and played it through in one sitting.
So, when Portal 2 was announced, I was super amped. Bought it brand new on launch day. No way on Earth I would have made that purchase without having played Portal 1, and there's very likely no way I would have played Portal 1 without having been able to purchase it second hand.
I just love how these big companies think that a used game sale is a loss of a new game sale. Buzz! Wrong! Same with pirated stuff. If someone is pirating the games, then they probably aren't planning on buying them, so there's really no loss of sale (not that I'm advocating pirating, just pointing out that the "it's a loss of a sale every time" concept is BEYOND broken).
His issue with people buying used games wasn't with people buying them out of the bargain bin months or years later, so much as it was with people who, instead of buying a game for $60 new, would buy it a day or 2 after it came out at GameStop for $58 used - not really the same as your Portal example. Then his perspective warped into 'all secondhand is eeeeeevil', which is obviously silly.
Once you've moved out of the 'brand new' phase, then what you spend your money on has pretty much no impact on the developers.
As to your "I just love how these big companies think that a used game sale is a loss of a new game sale" statement, there was an interview with one of the Quantic Dream guys talking about securing funding for their next project after Heavy Rain. In the interview, he said about how much money they made per copy of the game, then compared the games sales to the number of PSN accounts with the game on it, and it was something like a 40-50% mismatch between the two, meaning that many more people had played it than had purchased it new. He basically said that if only half of those people hadn't bought it secondhand, they would have been able to start on their next project right away, and have more money to do so with to boot.
I can't find the interview - I looked!
- but it (to me at least) confirms that yes, buying secondhand doesn't put any money in the pockets of developers.
But please don't hear me saying anything I'm not saying. Everything you said is correct - yes, trying the first game can lead to a sale for the second game, and yes, most pirates never had any intention of paying for it. But it's also not fair to completely write off the 'used game' problem based on your own experiences, because the issues aren't with one or two people doing it, but tens of thousands, and as with most economic things, the truth depends greatly on how your measure it, and what you're looking for, and almost everything is a little bit true.
And yes, I totally realize that the practical concerns of consumers have little to nothing to do with the concerns of industry, and in no way am I saying that buying used is 'immoral'. Only that with the way the video game industry is currently set up, a used sale (when a game is still widely available at retail) is less beneficial to the developers. After a certain point (6-12 months, I've heard), buying new makes no difference, because the stores are just stocking from what remains of their previously purchased stock, and won't be getting more. So it's a pretty limited timeframe I'm talking about.
Full disclosure: 98% of what I buy is secondhand, mainly because there's just no way I could afford all the stuff I want otherwise. I count on the people who aren't like me to keep companies afloat by buying things brand new
