I'd buy OMF: 2097 from gog for a few quid, even though it's available for free, if there was more content / bonuses. Even just a commitment to keep it working on future platforms.

Is that what you're asking?

To somewhat parallel what wpegg says: if they took a problematic freeware game and did the regular tweaks for operation under modern operating systems, then sure, that could be worth a few bucks.

I'd like to see GOG offer to "care" for more highly-desired freeware games (like the rejected Heroine's Quest), not to sell them though.

Like the recently-free'd Hi-Rez "Tribes" & co. games, if there's compatibility work or other value GOG can add there.

Why in hell would you want to pay more money for something? I fail to see any logic in this at all.