Currently, there are several heavy hitters on the Saturn I really want, and for the first time in a long, long time I'm thinking of taking the plunge. Some aren't too bad, but still fairly ridiculous like Shining Wisdom, Shining Force 3, and House of the Dead. But other's like Rayearth and Panzer Dragoon Saga make me sick when thinking of spending that kind of money on a video game, especially since both not that long ago were going for around half their current price.
Well, having picked up Rayearth for $320 just over 2 years ago now, allow me to offer my insights:
1) I'd been wanting a Saturn since I was 13, when my copy of Christmas Nights was stolen from my copy of Game Players & I was put off of using my Christmas money to buy the special sale bundle. Magic Knight Rayearth was one of the games I remembered reading about & wanting from back then.
2) Coming off of the holiday season always sees me more flush than normal due to extra Christmas hours, Christmas money, & birthday money. This particular year I'd also sold off some old anime as well.
3) At the time, at least, it was one of the better priced options available- and I had been looking for a few weeks.
For me, the combination of a (comparibly) reasonably priced option, extra cash, and a 20 year wait made it the right time to buy. Would I do the same for any game? No- at the moment the most similarly priced game on my lists is MUSHA, but I don't have a history with that one. Moreover, the fact that I had to look it up, that I didn't just remember I was interested, means I'm not ponying up for it anytime soon. For me, that's the biggest key- how much space the game takes up in my mind. Something that's lingered on the fringes of my thoughts for years or decades is far more likely to get bought that something I merely heard about somewhere. It's about playing the games, making memories, and having fun- not ticking off a box on some list of Brag-Worthy titles.
The second, but equally important consideration is cost- I don't worry too much about what a game used to sell for- games are popular culture, and popularity dies. So do consoles, chips, carts and discs. All of them will be worthless again someday, and I don't sell my games, so I just assume there is no value outside of what I apply to it. The question then is, not if I'm spending more or less than someone else, but am I spending an amount that I can afford & am comfortable with? I don't go into debt for games, so no credit cards- either I can pay for it or I can't. I also have to consider if there's someplace better I could put that money. I recently had a retropay windfall & damn near bought Keio Flying Squadron... but in the end, I decided to save that money for a possible trip to Disneyland with my fiance. It'll make more memories (there's that again), and if we don't end up going I can revisit the purchase idea later.
So, I suppose that's what you need to ask yourself- just how badly do you want it? What's your personal story with that game? Will buying it enrich your story? Would the cost hurt you? Can you better use the money on something else? It's up to you to answer these questions and figure out if yes, this game is what you want, more than the money or anything else.