This is an interesting question!
I have lists upon lists of retro games i want, but for the most part it’s just so I can keep them in mind. I live around shops that don’t have enormous amounts of stock I want, but they get new stuff in occasionally. So I like to visit fairly often and see if anything I want has come in. If the price is right, i’ll pick it up. I’m happy to buy loose carts (but not loose CDs!) although i prefer a nice box and manual if it’s not much more. For my favourites i like to have the box and manual, but i’m pretty selective about what is a favourite i think.
Every now and then I find something that isn’t really on my list but it’s so cheap I may as well get it. Or something that I thought i’d never find. Those kind of purchases become memorable I think.
Although I enjoy visiting the bigger stores that have lots of (usually more expensive) items, it tends to overwhelm me. I’ll find a stack of things I really want, but the price being what it is, i’m not likely to get 4 or 5 of them at a time (as I would if they were really cheap finds). It’s the same with online auctions. What do you buy when you could basically buy anything you want, instantly? I don’t want to fall into the trap of buying things i want just one after another. So I usually only buy from big shops or auctions when i’ve become fed up at not finding something locally, and when I’ve decided I really want to play that game right now. When I buy a bunch of cheap games, often they’ll sit on my shelf for months before i even try them out, but i’m ok with that. When i buy an expensive retro game, i want to play it right away, as if it had just come out.
I should point out, it’s only due to the existence of so many cheap retro games that i’d classify some retro games as expensive. For me, expensive means at or around the original price, and that’s something i’m happy to pay if I really want it. I don’t really consider buying stuff that has gone significantly higher than when it released. Particularly if i know it’s not even a good game!
When it comes to retro compilations, I will usually opt for the original if it’s reasonably priced. Sometimes I get swayed by a nicer box art on a re-release though! It can depend on system/controller or display preference/availability too. ie, recently I picked up Gradius Gaiden on PS1, instead of the much better value collection on PSP. I also find with collections, that I tend not to play everything as much as if i got them individually at separate times. They’re certainly nice to have, and convenient to play. But they can feel a little cheap in my mind for some reason.
Sometimes I even prefer to get the original over full remakes. Most recently i picked up Crash Bandicoot 2 & 3… still need 1! I’m not so attached to those games that I really need the enhanced presentation of the remake, when they still play fine as is. And i’d kind of prefer to remember them as they were; Impressive PS1 showcases, iconic character… it’s just not the same these days, when everything has amazing graphics, and Crash isn’t as big of a deal.
For my favourite games, i’ll often end up with both old and new versions. Original and compilation releases… In a few questionable cases, different region versions lol. Most of the time i prefer to play on the version that’s most memorable to me. Like SNES SF2 just seems right even though I have much better versions of it now.
I think the stuff like Wild Guns, Sega 3D Classics and M2 Shot Triggers are my favourite of the retro releases atm. Those original games are mostly unobtainable or undesirable in their original form, for one reason or another, and to have them come back and the same but upgraded is wonderful. Those are pretty high priority for me. When it’s stuff I never played originally, i’m happy to play these on newer systems at greatly reduced cost!