As far as I can figure out, the site began acquiring real content on Dec 23, 1999. The first two real-looking users that I can find are yiango and cinder_bdt. The next user created is the first truly active user, BBQ. The first real question was #!/usr/bin/perl T-shirts. It is hard to figure out what those early conversations were because there are a lot of missing nodes. For instance RE: RE: #!/usr/bin/perl T-shirts looks like it belongs in that thread but it was a reply to node 1371 which no longer exists.
The first well-known Perl person to join was chromatic. Of course at the time he was not a particularly well-known Perl person. In fact he was a co-worker of Tim Vroom's. This suggests that the site, while somewhat functional, was not yet public. Which fits with the fact that vroom once told me that the site was initially seeded with some real content so that the first outside users wouldn't realize how empty it was. But don't dismiss this early content. Internally created users like N-Wing are real people who still show up from time to time. And some look like interesting people - for instance nine9. Plus some of the early material they created actually was real - for instance "Stranger and Stranger" is certainly a real question. (There were a few other nodes as he tried to get the code in question posted for help - that is waaay too much work for fake content.)
This makes it hard for me to say exactly when the site was opened to the public. How do you tell the seeded content from that provided by outside users? Also they had a job for a while that would delete answered questions. (Why? My guess is that they thought that answered questions weren't interesting, and frequently asked questions would wind up in something like Categorized Questions and Answers. Things didn't quite work that way...) So a lot of the early content is gone.
But my best guess is that content from a week later is mostly real. For instance I don't believe Rhandom ever worked for BlockStackers. But I don't know for sure. The site was still under active development at that time. For instance NodeReaper's first victim was RE: POETRY!!! (Jan 9). Which was posted 1 day before the earliest user that I have met who was not internal to the development of the site (japhy). The first certified Perl luminary on the site was merlyn (Apr 25, 2000). I joined Aug 04, 2000.
At the time that I joined, the site already had a well-established user base and was producing a lot of good content. For the most part the culture was pretty good. However there was a clique that had driven away a number of technically competent people. As I have mentioned before, they weren't that fun to deal with. However they didn't last too long, in large part because it quickly became apparent to everyone that most users didn't agree with their agenda.
As a result I'd say that if you were familiar with Perlmonks in late 2000, then fell through a time warp to 2009, you'd find it a fairly familiar place. Sure, there is more material and history. The names of the active people have changed. But the culture mostly stabilized in that first year. While it experienced ups and downs, on the whole it has remained fairly good, and has lasted a lot longer than I would have ever expected.
Moving forward, I don't remember exactly when NodeReaper gained the ability to shut people out of chatter. However I can say for sure that Alex the Serb was the first person who NodeReaper was seriously used on. (I was actually the person who first pulled the trigger on him. I lost that ability on an extended absence from the site...) Alex's issue was quite simple - he was a Serb who was outraged at the American intervention in the Serbo-Croatian war. And was outraged at anyone who he even suspected did not see the US involvement as a bad thing. And was prone to expressing his outrage with long rants and much swearing. While I completely understand how upsetting it is to have your home bombed, his mode of expressing his feelings wasn't exactly what we wanted in the chatterbox...
However as successful as the site was as a community, it wasn't so successful as a business proposition. As a result in this poll vroom indicated that he was losing his job. This happened in April, 2001. The addition of an Offering Plate didn't quite cut it. Luckily for us vroom continued donating time to us after he lost his job. Then YAS stepped in to keep the site going. They gave us to The Perl Foundation when that was spun off later in the same year. The following year Pair Networks began hosting us. Over time maintenance moved from vroom to a team of volunteers, with tye and jdporter being among the most notable contributers.
So if you've ever wondered whether The Perl Foundation actually does anything for the Perl community, well now you know. This site nearly went away like so many others in the dot com crash. It is only due to their help and the generosity of Pair Networks that it still exists.
I could easily go on. For instance I've said nothing about some of the great content that people came here for. But this post is long enough already, so I'll leave it as what it is and let other people share their experiences/views of the past.