The games are all fantastic, and the series has done nothing but improve since the days of Red/Green. Each game's mechanics are better than the last with VERY few exceptions. Gen 1 started it all and is my favorite to play through in a weekend, just because it is relatively short and limited. Gen 2 unbroke the Psychic type, and gave us a really long and satisfying experience (complete with going back to Kanto and even fighting Red and Blue, and the introduction of shinies). Gen 3 made competitive play more interesting by reworking EVs and IVs, it gave us 2 interesting villainous teams, and it perfected the Battle Frontier concept. Gen 4 gave us the Physical-Special split, giving us new incentive to use previously-terrible favorites, there was a big new post-game area, and backwards-compatibility was restored. HGSS vastly
improved the gen 2 experience overall (and gave us this
). Gen 5 stepped up the writing standards, made battles more dynamic and less tedious, introduced a record number of new Pokémon, and really upped the deluxe version standard with sequels.
Now as personal preferences go, I must say that I am totally biased toward gens 1 and 3, for personal reasons. I've played through those games more times than I can count (well, about >40 or so for gen 1 and >15 for gen 3). Those games have the biggest dose of nostalgia, even though I recognize their flaws compared to later games. In the end, I'd say I am all of the above. A genwunner, newgenner, Hoenn baby, and truegenner all rolled up into one. I recognize the games are all great, they are getting better (slowly), and I have nostalgia for the older titles. Neither gen 1 or gen 3 is the "best" by a long shot, but they are what I would be the most eager to pick up and play again. I have huge respect for gen 2, gen 4, and gen 5, but in different ways. What annoys me the most are the people who argue that Pokémon is going downhill since Gen 1/3. That's simply not the case. There are more than enough new Pokémon in each generation for me to find ones that I love, and alternatively ones I love beating up when I get the chance! In the end, the flaws are drowned out by the legendary variety in gameplay options. A few subpar Pokémon each generation does not make for a subpar game, and any "bad" Pokémon design is met by at least 10 great ones anyway. There's way too much about the series to love to get bogged down by nitpicks or minor differences in opinion.
Does that answer the question?