Can’t speak for the rest of my generation, of course, but here’s my experience:
Drummania: $50 + shipping
That’s the original Drummania, complete with jerky scrolling, ridiculously pathetic options, and screwy scoring. And not that many songs. I actually could’ve gotten this about $30 used a few years ago, but I was young and shortsighted (and lacking a steady job and not completely sold on Drummania just yet…) and passed it up. Hey, it could’ve been worse…my Toys 'n Joys wanted $73 for it (and it was a scratched-up-to-hell used copy).
We Love Katamari: approx $23
Yeah, I was pretty insistent on the sequel; it’s the one that had the “turn off infinite time” code (don’t ask). Whole bunch for sale for reasonable prices on Ebay, but there was competition (ooooh) for them, and I admittely reached for a higher-priced, lower-demand seller.
Pop 'n Music 4: $50 + shipping
This is the Playstation version we’re talking about now. I didn’t see the PSX PoMu games in any store, and they’re out of print now, so it’s not like I had much of a choice. I was able to get the first three games for less than $80, so I might’ve been just a bit unlucky here. Nothing out of the ordinary.
Soul Blade: $25
I’ve played this for about two months so far, and lemme tell ya, this is not a $25 fighting game by any stretch of the imagination. (In fact, the only reasons I paid that much were 1. stores all out and 2. cutthroat Ebay competition.) The controls are clunky, the timing for the Critical Edges is aggravating, and the less said about the graphics, the better. Didn’t even have an option for the original voices, for crying out loud.
Street Fighter 3 Double Impact (Dreamcast): $20 + shipping
Ah yes, the old Street Fighter 3s. On a long-defunct system. And no instructions or box art.
Tekken 5/Gran Turismo 4: $35 each
First off, I want to say that I always thought both franchises were overrated. I find Tekken’s system no fun at all (cf. to Fatal Fury or Samurai Shodown; it’s not even close) and Gran Turismo needlessly complex (there’s a reason most racing game programmers don’t go for realism, y’know). Okay but definitely not great deals at $35, certainly not secondhand.
Vampire Night: $20
Blockbuster Video “bargain clearance” item. It’s a poor man’s House of the Dead, and the dialogue is only slightly less annoying. Worth at most $12 (especially since the excellent Time Crisis 2 goes for like $15 now).
Time Crisis: Project Titan/Ninja Assault: $50 each
The first one’s actually not impossible to justify, as this was an extremely obscure title that I searched up and down for years to no avail. (That it’d turn up at Toys 'n Joys out of the blue a few months later is something I could’ve never anticipated.) The latter, though was a real reach…c’mon, it’s a Namco game, for crying out loud, it’s was never in danger of completely vanishing. Sure enough, less than a year later, I’m finding it for $20 and $15 in the stores I go to all the time.
On the other hand, I’ve also found lots of real bargains: Beatmania IIDX 3rd and 4th for a combined $75 (expect to pay at least double that now), Dynasty Warriors 5 for $20, NBA on NBC and WWF Royal Rumble for $1 each, Pump It Up for an incredible $10 (the same as what I paid for that execrable Mad Maestro, for crying out loud), WWE Smackdown vs. Raw 2006 for $10, Fighting Vipers 2 for about $16, and many more. Rare or not, getting a good price is still largely a matter of luck. (Or good connections. But mainly luck.)