We didn't have as much Pokémon as we do now, so when it comes to completing PokéDex and other tasks of the like, I could imagine it to be a lot easier.
Sadly, though, I've never managed to take it on. Although I did think about it every once in a while, I didn't have an additional GameBoy and nor link cable. Of course, one of my cousins did have them and I could've easily traded in order to have my PokéDex done, but sadly, she lived far away, and only got to see her once every weekend, when her mom used her off to our house before heading to work. Sadly, she never bought her GameBoy with her. Though, I'm sure she would've if I'd asked. Wasn't exactly focusing on completing my Dex back then, anyway, so it's not such a huge deal.