retrorealms: Much of the penny-pinching is because people are critical toward specific editions of released games, or critical of the studios releasing the games - GOG simply gets caught in the crossfire. I'm guilty of that myself at times.
I am as well.....still, let's be honest a bit here(or more honest I mean).....some of us will find ANY excuse not to buy a game and add to our ever growing backlogs, just as some pirates will often find any excuse not to buy a game/other piece of media.
retrorealms: However, when it comes to GOG itself, idealism kicks in with many users of this platform because people truly believe in DRM-free content and are willing to put up with things they would not otherwise put up with. The idealism of the people making up the GOG community is the main reason why GOG has managed to compete with Steam and stay afloat all these years. I would myself definitely support any crowdfunding venture by GOG, I would happily give some €10 for an overhaul of their website and another €10 for a Linux version of the GOG Galaxy client, even though I haven't used Linux myself in years. I think that many Linux users currently not using GOG because of its lack of Linux support would also happily contribute. If it 's a matter of funding then it's up to GOG to initiate these crowdfunding initiatives - if they fail then at least we will all know that GOG isn't the one to blame for lacking features ;)
The problem isn't just how many might contribute if such were done, but the disparity of donations.....ever see a coin box for donations? Most of it is usually nickles and pennies....as in the least people can give in most cases.
Yes, some who donate do so to a high degree, but they are fewer and more far in between than those who give little or not at all.
Now i'm not saying such efforts wouldn't amount to much....we'd need to try it and see...but until then all we can do is speculate and from what i've seen of human nature in this regard the likely outcome(from looking at such) isn't as good as I wish it could be.