I'm probably a Hoenn baby, though I was a fan of Pokemon before I even got my first games, which were Emerald that I bought, and LeafGreen that a friend traded me for Kirby and the Amazing Mirror. Because of those two games, Gen 3 is easily my favorite. Hoenn was a pretty fun region, and I didn't really mind all the water there. My only gripe is that whenever I go back to it, it's PISS EASY unless you Nuzlocke it. Starting a new playthrough, Swampert, Swellow, and Magneton are literally all I needed to get through the game, with a couple HM slaves and death fodder thrown in. Marshtomp/Swampert takes care of Roxanne, rapes Wattson, destroys Flannery and takes electric attacks for Swellow, Swellow/Crobat deals with Brawly and takes care of the grass types Swampert hates, and Magnemite you catch at New Mauville the first time you visit there, get Thunderbolt from Wattson immediately after you catch him, easily train him on the water routes till he evolves, then destroy Winona and Juan.
The Elite Four are a joke too, and more annoying than difficult. Hell, that can go for the majority of the trainers in the game, and it doesn't help that everyone and their dog carries Double Team on their pokes (Thank god for Shock Wave and Aerial Ace). If they ever decide to remake these games, they really need to up the diffulty and lengthen the game a bit.
Other than that, as a kid, I picked Blaziken anyway, so it was a fun region, catching legendaries was epic, the music is some of the best in the series to date, rebattling gym leaders was sweet, Battle Frontier was nice (even though hax fucks you over) and overall, it was an awesome experience.
Kanto was pretty dang awesome, and has my favorite Elite Four, simply because they're the ones I lost to the most. I couldn't get through the game with just three strong pokes either, I needed at least 5, making it harder since I was a bit underleved at times. Overall, I like the difficulty as well as the Sevii islands that can be explored afterward. Oh yeah, and the Elite Four actually toughens up after you beat them and doesn't just stagnate like they do in RSE. A friend sold me the original Red so I can see the comparison. Played like 30 minutes of it before I said "These graphics suck" and went back to LG (I was 10 alright?). Even playing it right now, I consider the remakes to be superior. A lot of things were fixed for the better, but it still kept most things in tact. Psychic was still powerful (no Dark types and only 2 steel types, which weren't even that common) and the physical/special split didn't happen yet, so it still felt the same more or less. I like it a lot more than Emerald. I lost my LG a while back though, and bought FR to replace, which I also lost, but just found yesterday. I forget what my team was since it was years ago since I lost it, but it's gonna feel awesome when I turn it back on again once I head back home and find my SP.
Gen 2, I thought was amazing. Mostly because I hadn't played it and there was no remake at the time, but I so wanted to. When I heard you could get 16 Gym badges and go back to Kanto, I was like holy shit. Also, there were a lot of Johto Pokemon I wanted but couldn't get. HGSS came out and made that a reality luckily, and I'm playing regular Silver right now. I really start to miss the 3rd gen movesets and TMs though. Magneton being forced to use Thundershock for STAB the entire game REALLY sucks.
Gen 4 really stepped things up. It's where I started competitively, so of course I look fondly on it. The physical/special split was fucking genius, and I explored EVs and natures more, which were also in Gen 3 but I really didn't give a shit as a kid. My Careful Blaziken was still awesome to me. Nowadays, that nature would've pissed me off. Sinnoh is indeed my least favorite region though, but I will admit it's the most difficult. Replaying Platinum (fuck DP, they're garbage in comparison and I can't go back) is tough. Compared to older gens, where it's slim pickings for good and viable pokes in game, there are so many useful pokes that could work for my team in Platinum I end up trying to train them all, and as a result, end up underleveled and the game becomes a grind to get through.
The Elite Four was okayish, but Cynthia was a bitch. Easily the hardest and sexiest champion. She's surprised me on too many occasions (Heh, I'll Thunderbolt her Milotic. Easy 2HKO. Then you realize the fucker has Mirror Coat). The Battle Zone was pretty cool, but 4th gen also brought us the GTS and wireless wifi battles and trading. In the GTS, legendaries and past gen starters were in super high demand back then. Got a Lv. 100 Kingdra, Heracross, Milotic, and Shiny Ho-oh from just breeding Torchics. Aside from the douchebags who like to ask for Lv. 9 or under Zapdos (Seriously WTF?), the GTS was very innovative.
As I said before, HGSS were a dream come true, and I love everything about the game and it's probably my second favorite. I gotta admit though, the new abilities and physical/special split make things a lot easier. I mean, you get Shadow Ball super early. Teach it to Gastly and it pretty much one-shots anything that doesn't resist it, and once you fully evolve it and teach it Sludge Bomb, it can carry you through most of the game. Scyther with his Technician Wing Attack and Heracross with his Close Combat are the same way. Not to mention the Red Gyarados outclasses your Feraligatr when you catch it. But still, I like it a helluva lot more than DPPt But the best thing, the greatest thing about 4th gen, was the Pal Park. Remember that Lv. 100 Venusaur from LG? Well bring him on over into 4th gen and just fuck everything up with its Quirky nature and super pro moveset of Sleep Powder, Razor Leaf, Sludge Bomb, Frenzy Plant -- just like the old days! God that was fun.
5th gen, I gotta say, I wasn't super impressed. I admire GF for trying to take a deep approach to storytelling. Good effort, but you know, nothing special. Evil team, summon legendary, blah blah, seen it twice already. Wasn't expecting that much anyway. Just liked having the new pokes and battling competitively again, since after the Elite Four, there really wasn't much to do besides fuck around in Battle Subway, which allows Excadrill so it's not that much of a challenge. I haven't bought Black 2 or White 2 though and people really seem to love that game.
All in all, I like every gen, simply because I like Pokemon period. I respect the newer ones just as much as 3rd gen, since they still stay true to the formula. I'll categorize myself since in everyone of Basileus' categories, he paints them in a negative light. There's no middle ground, you're either one thing or the other.
And Basileus, you say you're afraid of there being fights in this thread, yet you're picking apart every person's opinion you don't agree with. Just respect it. If you're gonna disagree, at least be civil about it.
God damn that was a lot of text.