Has it really been that long? I remember hearing about the original IL-2 release and being not that interested in the Eastern Front air war at the time. Why I don't really know anymore because it's now possibly the one I find the most interesting.
I eventually got interested anyways and played the IL-2 demo on my Pentium II with a GeForce 2 GTS card. Those were the days
Grabbed Forgotten Battles fairly soon after that came out and went through every patch and iteration since then.
As for online... I can't remember the server names but I remember my first online experience was with the then uber Hurricane Mark IIC where I shot down a couple of guys (and was shot down frequently myself). I then started flying the La-7, the Bf109K-4, and later the P-47 and FW190 when I got bored of the usual stuff at the time.
Somewhere along the lines I heard about a third party effort to bring the Tempest to the game and I was very excited (for years!) waiting for that to happen. So glad that it did. Disappointed we never saw a Typhoon but alas one dream accomplished is enough.
It's been a remarkable lifespan for one product. It's not dead yet and it's legacy lives on in Rise of Flight and IL-2: Battle for Stalingrad.