I've only bought a few games in recent years. Cataclysm and Pokemon: White. Cataclysm/WoW in general I play more than anything, since it's 15 a month and it's a good source of entertainment when I have free time. It's affordable is the main thing, where as I can't really afford all the new games that come out. (and I wouldn't ever dream of trying out a new MMO like SWTOR) Luckily I've got friends that buy me games for me on occasion (SG got me Minecraft way back in the day. A friend of mine "bought" me Portal 2). Sonic Generations I made a rare exception to not renting games and found a blockbuster around here. And the I played Heavy Rain recently because my roommate happens to have a PS3.
So much of my money goes to either bills, rent or food, that's it's rare I get to really splurge on anything. If I do play a new game, it'll just be renting and that's very rare. Single Player games are even MORE rare for me to bother with unless they are a big deal to me (like Generations). Multiplayer games or games that have multiplayer stuff such as WoW, Pokemon, Smash Bros, Portal 2, whatever, area lot more appealing cause then I can include gaming in my social life.
There are a lot of games I'd love to play. But I just don't have the time and money anymore to play them. Which sucks cause I do feel like I'm missing out. But thems the breaks. I have a lot of TV that I watch too, and honestly that takes precedent (I just recently got caught up on all 8 seasons of House so there's ANOTHER show to add to my TV watching, but because of my marathoning it, I'm now behind 2 weeks on all my other shows like Parks & Rec, Adventure Time and The Office).
I didn't include iphone games on there because they're either like 1-3 bucks or get gifted to me (usually gifted)
If a game comes out that really does something different I will take notice and try to get in on it. Minecraft did that. The Portal games did that. Team Fortress 2 did that just by how the art style is. Heavy Rain. Spore (which honestly ended up being more of a disappointment than anything). If they ever release Half Life: Episode 3... There's a game coming out soon that looks really creative and I probably will spend the money on it. Quantum Conundrum. Look up the videos for it, it looks really neat.
edit: As for the main topic, working hard for the money ITSELF feels way more satisfying, but the stuff you get with that money doesn't feel any more or less satisfying than it normally would.