Only with 2 friends, and they didn't really live near me, so we arranged a meet up on a Saturday back in 1999 to do some trading, and also starting over to have all 3 starters, so first we traded all the pokemon we wanted (the exclusives, the link-cable evolution only, etc) and then we started various new files with one cart to get 3 starters for each or something like that. It took us the whole day and we still couldn't do all we wanted. In fact, both my friends completed their dex, but I didn't, I was missing something, can't remember what, and anyway I restarted my file, now with 3 starters and a bunch of pokemon exclusive from the Blue version that one of my friends had (me and the other kid had Red).
Also, the night before, I stayed awake until like 5 AM playing on Safari Zone, because none of us had Tauros. I finally catched one, and it was thanks to that that my friends could complete their dex.
Years later I got Pokemon Stadium with the transfer pak and got as many starters and rare pokemons as I wanted lol.
With gen 2 I had more friends into it, I remember trading pokemons and mystery gifts, and doing battles a lot