This is by memory so some of the details might be a tiny bit off - feel free to correct me

In 1995, I was going through pilot training at Laughlin AFB, TX. My internet connection was a long-distance dialup connection to netcom in San Antonio, for about 15 cents a minute. FWIW, my largest phone bill that year was $1100 and I also spent a couple of hundred on WarBirds that month too.
I had been playing microsoft flight simulator since high school and enjoyed the heck out of Chuck Yeager's Air Combat, but as my real life flying skills increased I wanted a bigger challenge. I'd heard about AW and even tried out the boxed game, but it never clicked with me and I didn't have any money until 1995 anyhow. Then on alt.games.pc.flight-sim, I heard about this cool new game you could download and fly online for free. Getting online was a bit of a hack since it required a telnet connection (the tcp-ip connections everyone uses now were still almost unheard of at home), but on my old 386 DRx2 based system, all things were possible. I had a shiny new degree after 4 years in a computer science and engineering program, so whacking about online was second nature. I already had the thrustmaster FCS/WCSII programmable setup, so I was ready for the game. This was in mid 1995, with CK .8something if I recall correctly.
At the initial game setup, I couldn't think of a good ident so I chose "suck" because I'd read some newsgroup threads about people showing up and bragging that they were "good at flightsims" and I wanted everyone to know I didn't think I was so good. It turned out to be a good choice even though after my second day online my K/D never dropped below 1 (so I really WAS "good at flightsims"? LOL. I still suck, just ask Drex.)
My first online experience was a mixture of luck and pure dweebery. It took me less than an hour to figure out how to get off the ground in one piece. Once airborn, I proceeded to shoot at all these guys with red icons because red guys are bad, right? Well, it turns out that all new players started out flying for red, oops. After 3 fairly quick kills I read the text buffer, apologized, and set out on my way to find some real opponents. The terrain at this point was pretty flat, with some hills but definately not what you'd call "rolling". That came later.
I met up with a guy with the callsign "grdr" (for grinder), and he gave me my first virtual BFM lesson. I learned firsthand how flat turns at the merge don't work, so we fought and I died. We flew a lot against each other and at some point I started being able to hold my own. I switched countries to fly with him, and we ended up making a pretty good team. He'd get kills, and I'd scare people off of his 6. I never minded letting him get the kills and I can say my greatest online flightsim skill is being able to help others survive and get their own kills. That's the only reason Drex and I were any good at the dueling tournys - I focused on keeping us both alive so he could do the actual killing, and it worked just like it did back in 1995 winging with grdr.
Since I was living in the dorm and had some extra cash to spend, I ended up buying a screaming fast ZEOS pentium 66 with a full 32 meg EDO ram. At the time, 66 mhz over 60 mhz and 32 over 16 meg ram, let alone the EDO, bought a huge price premium. I got the ZEOS with all the bells and whistles because it was hands down the fastest prebuilt system on the market, plus it had the magic touch - an S3-968 based video card. That was important at the time because CK temporarily used a graphics engine that used S3 specific hardware to allow for some neat rolling terrain at what was then the amazing resolution of 640x480. Although the graphics engine changed and we went to what turned into WarBirds, that S3 video card remained about the fastest on the market until the Tseng ET-6000 hit the street.
Near the end of 1995, I found I was going to be assigned to the F-15E so I changed my ident to "eagl" and I've kept it ever since. I even dueled one person to keep the ident, because he was using "eag1" and the font in WB at the time made the 1 and l look the same. I won a best 2 out of 3 duel, and he was really cool about the whole thing and changed his ident to something else.
I resisted the move to the windows version because the dos version flew better. Oh yes, WB was a DOS APP! For a long time too, since the dos version really did fly better than the windows version for a long long time. Looking back, I can't believe they developed both the dos and windows versions for so long. Technology marches on, and going to a windows-only game enabled a lot of things like real TCP-IP connectivity (even though the base connection was still essentially telnet for a long time) and lots of other features that kept HT from having to code for specific hardware.
At some point Tone did some coding, and that had mixed results. Tone's Wildfire / HQ was an interactive text "bot" that could act as an intelligent message handler, provide realtime scoring inflight, track squadrons and create virtual radio channels by accepting text commands and sending private messages to anyone on the virtual channel, etc etc. It was a perfect ground control executive officer, but it relied entirely on parsing the text from the game and a database on his own machine, and this had multiple ramifications... Ultimately the telnet and parsable text interface went away and HQ died with it. In the many years since then, nothing has come even remotely close to the functionality it provided players and scenario managers.
The second thing Tone (and several others) did was create Roger Wilco, a voice app that ran quite well in the background. RW had hooks into MSIE, various messenger services, and basically sparked a dozen competitors that eventually crowded RW out of the market. Too bad, but of course AH has voice and that might not have happened if Tone and the crew at Resounding hadn't proven the technology. They did radio-quality voice over a 56k modem and it didn't cause warps, amazing.
Anyhow, that's a bit of what I remember from way back when. Hopefully my memory isn't too inaccurate or biased.