I'll enter for the $9.99 GOG, please. Since I'm not sure whether or not you consider me a regular, plus I have some free time lying around, I'll answer some of the questions too.
1. Usually I don't have these type of moments, but I did score one in System Shock 2 fairly recently that I thought was pretty cool. I was in a regular room, when suddenly a couple of Cyborg Assassins popped up from nowhere and started to make short work of me. I quickly jumped and crouched behind a desk, where they couldn't see me and healed myself quickly. Once I had done that, one of the Cyborgs was approaching the desk...I pulled out my laser rapier, slashed him in the knees, then jumped up from behind the desk and ran to the opposite wall, drawing away fire from my position; then I went against the other Cyborg, slashed him to pieces while he was also blocking fire from the other Cyborg, and then I switched to the pistol in mid-jump to another desk and headshot the remaining cyborg with one bullet. After that I had to take a moment to observe the scene and thought to myself "wtf just happened". Pure reflexes and intuition = great sense of accomplishment / Neo-like feel.
4. Carmageddon was surely one; I used to play it a lot in the early 2000's and really liked it, but had since misplaced my disc. Also, this meant that Reincarnation was going forward since they already provided something back from my initial pledge. As for the new GOGs...well, honestly, there aren't many of those. For some reason, the new games GOG manages to take under their wing is usually stuff that personally doesn't interest me that much, plus they're often indies that fairly often drop in price quite quickly. But there were a couple: Miasmata for example was interesting from the start when it hit the frontpage, and later when I got it, it became one of my favorite played games this year. Zafehouse: Diaries looked really interesting too; and while it was pretty fun to play as well, it does get old kinda quick, plus sometimes it feels too randomized. FTL and Hotline Miami were also really great, but this I found out only after I had purchased/received them; I didn't have any actual expectations for them, just wanted to see if they're good games, and they were.
5. I do know about the GOGwiki, and I believe I should still be found there too. I joined it in preparation for wpegg's "Nasty giveaway: Revolutions" giveaway.
Thanks for this giveaway JMich, and congrats on the upcoming 4th pointy!