1. Amiga
2. Dreamcast
3. Commodore 64
I say Amiga first, because I think it has a lot of historical significance, especially in Europe, and while emulators and roms aren't uncommon, they aren't the easiest to set up, and doesn't give the games the historical context I think a GOG release would (both with a preconfigured GOG wrapper and great background info on the GOG site), and I think the Amiga, even more so than the C64 influenced the modern PC games. It was the first common home PC with rather advanced graphics and sound hardware, and was a valid competitor for the IBM PC up until the mid 90's, with many great games in it's library.
I'd especially want to see some of the Psygnosis games which really utilized the graphics and sound capabilities to it's fullest (while possibly lacking somewhat in gameplay), and games like Gloom which I think is one really interesting Doom clone.
I put Dreamcast second. Personally I'm not _that_ interested in the system, and probably wouldn't buy many of the games, but it was an important system, which had a too short life. It would really deserve to have it's titles re-released on GOG or modern consoles.
And well, I also chose the Commodore 64. I have no personal connection to that or any of the other machines I mentioned, but the C64 glory days were a couple of years before I was introduced to gaming, but still, it was a very influential machine, especially when it came to music and sound, and how it gave birth to most of the demo and cracking scene. Possibly not a part of computer history that publishers want to give too much attention, but demos, cracktros and demoparties were really important when it came to computer generated art, and several demo groups later became important in the gaming community, many as developers (Remedy was founded by former Future Crew, Starbreeze created tracker sequencer programs, many vgm soundtrack composers are former demoscene musicians, like Alexander Brandon, Jesper Kyd and many others).
Sorry, this post went on a bit too long. :)