I've been perfectly ok buying all the Saturn games I've purchased, which most of the good ones aren't cheap. I've purchased PDS, MKR, Saturn Bomberman, Dragonforce, SF3 and I don't regret any of these purchases. Also shelled out a decent sum for Snatcher and both Lunar's on the Sega CD.
Just think, people who buy games like Call of Duty or Battlefield and buy the "season pass" already pay over $80 for those games. I'm not sure what games I may have paid $80+ for if any. I don't recall any really big ones but then again it's only more recently that various games have gone up in price so much. But you do bring up a great point about emulation and flash carts. When your options of what games you can play are "every game for the system" you can be overwhelmed or too indecisive or just don't stick with games. For most of us we only had a limited selection of games to play at any one time. And beyond that we could maybe rent from a store or borrow from a friend. So you're going to play those games a lot and get the most you can out of them. But when with emulation/flash carts you suddenly have everything you lose that incentive to play through games since they didn't cost you anything and you have so many other choices. So you really need to make an effort to seek out games and give them a real chance. It's too easy to just move on from one game and start another and then another and never finish any. But it's something you can deal with if you realize what you're doing. Emulation and flash carts are great if you use them well.
That's something I came to realize when I had my raspberry Pi up and running, I had access to everything but I wasn't PLAYING everything. It was just the same games over and over and over again. The perpose flashcrarts will serve me will be to play Romhacks, maybe some stuff my friends and I cook up, and those games that are just too expensive to feasibly obtain. My Mega Everdrive will likely comprise of almost nothing BUT Sonic Rom hacks.
Megaman X, X2, X3 and Conker's Bad Fur Day. Megaman, because I loved X-X3 the most out of all the series. Conker, because tweaking Mupen64Plus, 1964 and project64 can get close to the N64 experience, but I can't get it quite there.
Steel Batallion for the original Xbox with the controllers, never had the chance to play it and would buy it just to calm my curiosity, and maybe try to get it working on PC with other simulation games.
I'm fan of Fatal Frame series and found that this games are the ones of the most expensive items in japanese yahoo auctions if you go to xbox game section. Someday I'll buy a new Fatal Frame II (that is the only part of series that missing in my FF collection). It will cost me may be $300 but it's ok for me because I'm crasy Fatal Frame fan. And may be I will open it.
Probably most any (US) Dreamcast game, and occasionally I'll pay over $80 for a special edition of a new game (usually with some cool physical statue or something). If you don't mind the Japanese version, you can get Rez on eBay pretty cheap, I think I just paid like $25 for it. The 360 version is on the Qubed disc with Luminies and EEEE for dirt cheap too.
Prices of second hand games have gotten out of hand TBH. Some are just too ludicrous beyond the point of reason. If people would stop paying these prices, they wouldn't sell and would hopefully drive the market prices down. 100$ is where I draw the line. I won't pay more than that generally. There are several games I love that I wish I had never gotten rid of, even when they were dirt cheap that are obscenely priced these days. Makes playing these games more of a financial hurdle than it needs to be because of self inflated value and greed. And people wonder why bootlegs have become so oversaturated.
Buy Japanese, On average for about 8 Famicom or Super Famicom games it's about $200 granted there's at least 1 $60 game in my buying sprees. But Japanese versions tend to be on the cheaper side.
I meant to reply to this before, but I forgot. I have the same problem you're talking about, but with physical games. I have hundreds of games, so sometimes it's hard to decide what I should play. Most of the time I have at least one game I'm trying to finish, but sometimes I feel like playing something else - and it's hard to decide, because there are so many choices.
I've had the same trouble as you guys as well, but when I noticed it happening I tried to make up a couple things to help. - try to limit the RPG games to playing them one at a time, keeping track of multiple stories is so difficult and you strive to actually finish it so you can move on to a different one. (this doesn't count for ones I've beaten) - If I'm really stuck, pick a system, then randomly pick a game. Whatever I pick I have to give it a fair chance. - Have weekly/monthly etc. "game I never play night", where you purposely look for a game you either can't remember or haven't played in a long time or rarely played at all. Try to give the game a good long chance, if it's really not great, you can only move onto more games you never play.
Back on topic of the OP, I've bought some expensive games. I got Radiant Silvergun recently, which was pretty expensive (worth it though, I think). I also have a Sega Model 3. I used to have a copy of Espgaluda, but I sold it for about the same as what I paid for it. I have a lot of games that weren't expensive when I bought them, but they've since gone up in price a lot.
It was a BIN, but it was actually $36, plus shipping. Though the Qubed disc for the HD is findable under $10 on eBay.
I ended up getting Rez: Inifinite, since they released it on Steam I was able to play it. Area X is so god damned beautiful. I'd still like to get it on Dreamcast, but I'm in less of a hurry now that I can play it in the mean time.