Personally I'd rank them as 5 > 4 > 2 > 3 > 1 > 6 > 8 > 7
Gen 5 is above the 4th basically because they perfected the Special/Phys Attack Split that was introduced with Gen 4 + Gen 5 was absolutely ruthless in terms of difficulty. Especially the rematches and the post game. Only Legends Arceus featured a fight that I would deem more difficult and that isn't even a mainline entry xD
Gen 1 is only so low because it is held together with duct tape and gum. The 1/256 Bug alone is a huge pain. Or that ghost is weak to psychic and not the other way around.
(Gen 2 is only above Gen 3 due to massive nostalgia. Playing Silver late night on roadtrips on my green gameboy color was something special lol)