>>48147181I started with Gen 1, and Gen 2 is objectively the best. Even as a kid, I could tell Gen 3 was a downgrade. The first four gens were honestly made better by all the peripheral games that started going downhill around Gen 3 as well (Stadium games to Colosseum/XD and PBR). I enjoyed Gen 5 for what it was, but it was the first time I felt like Pokemon was starting to lack soul. The cancerous new Pokemon from Gen 5 certainly didn't help. Gen 6 was the first time I felt like Pokemon had been reduced to babby-tier difficulty. I liked Gen 7 better, but only because I thought the story and NPCs were superior to Gens 4, 5, and 6. The game itself was still pretty easy. Gen 8 is now back to Gen 6 levels of difficulty, if not even easier.
tl;dr thank God for the virtual console games. Gen 1 will always be the most replayable, and Gen 2 will always be the comfiest.