Looks like I'm one of the oldest posters here, alongside thraxman and Mr.Mumbles. First purchase was Sacred Gold on Nov 11, 2008, followed a month later by Gothic and Arx Fatalis. Currently at 337 games purchased, and I'm not going to count up what I've spent, as I'll either end up having to re-evaluate my spending priorities, or feel like I've ripped off GOG given the amount of entertainment they've provided me.
Crosmando: So what was early GOG community like? As in the first few years.
It was a very... focused community, with most of the early members being a combination of folks who's grown up through the 80s with classic games, and those having a major axe to grind with DRM (at the time DRM was pretty ubiquitous and it was also quite difficult to get functional versions of older games). For the first few years it was a pretty small community with a dedicated group of regular posters who were actually a pretty cool group to converse with regularly. The release of The Witcher 2 in 2011 was essentially the Eternal September for the early GOG community, resulting in an explosion of new members. The fake shutdown publicity stunt in Sep 2010 also drove off quite a few community regulars, and the combination of those two events resulted in a pretty significant shift in the GOG community (changing from a small, insular core to a wider but less regular community). For those who aren't aware, The Witcher 2 actually contains a reference to the fake shutdown fiasco and the following GOG apology.
I actually had a chance to meet some of the key GOG people in-person at a meetup during the GDC in 2014, which included founder and CEO Marcin Iwiński, as well as a well-known community manager at the time with a distinctive hat. A lot of us were pretty awkward nerds at the time, but it was still really neat to meet many of the key people who had made GOG happen and drove quite a change in game distribution at the time (before GOG pretty much nobody was interested in distributing older games, and DRM was just regarded as a standard part of game releases that wasn't going to change).