Gen I and II were good gens for their time. Playing them again now I probably wouldn't enjoy as much because of how dated they are.
Gen III was my favorite generation ever. Had the best starters (Mudkip being my favorite), great music, tropical region, introduced alot of dual typed pokemon, great gymleaders, felt more adventurous than the previous games, introduced pokemon contests and introduced double battles. Hell even the spinoff based on gen III were good like the mystery dungeon games and pokemon colosseum/XD.
D/P was slightly better than gen III imo. It introduced new baby evolutions which I really didn't give a fuck about, slightly better EV training, a badass female champion in which we never had up until now, introduced wifi battles which was fun as fuck and I used to upload them to YouTube back in the day. Mind you D/P did have its faults. Surfing was such bullshit that had it not been for how bad it was I honestly wouldn't had minded replaying the damn thing. Imagine seriously trying to play Gen III with the speed of D/Ps surfing speed. D/P near endgames had terrible balance issues.
Platinum was a huge improvement for sure. Better gym puzzles, gym leader animations, pokemon got more updated sprites, much better endgame and even brought back the fucking battle frontier! Giratina and Shaymin new forms were pretty cool too.
HG/SS hands down is probably the best damn pokemon game gamefreak ever made with little to no flaws that I can remember. Pokeathlon was actual fun content that wasn't boring as fuck like Gen III and Gen IVs pokemon contest, great music accompanied by beautiful sprite work, very good QoL improvements like having walk/run be a toggle button which was great before you finally got a bike, return of apricorn balls, brand new moves for older pokemon (then again this is true for previous games aswell), brought back platinum battle frontier,, and the best part...you can walk with every single pokemon dating back to Gen I. That was honestly the most ambitious thing that was added into HG/SS and many fans loved that feature including me. The game didn't even feel like a damn remake really and you could see that they put in a fuck load of effort into it.
B/W was...kind-of sorta on par with Platinum but not as good as HG/SS. It had an actual good story with characters I actually cared about, seasons were added which made the overall region more unique, an interesting antagonist in Ghethis (atleast in B/W), enjoyable final battle with N, kick ass music hands down and probably had the best music out of all the mainline titles. This generation had all pokemon fully animated which was fucking
HUGE! Now for the negatives: pokemon designs were honestly a hit or a miss, region layout was kinda...mediocre atleast compared to previous titles, at times the game was too easy by including doctors/nurses in caves that would heal your pokemon to full health, no return of the battle frontier and hardly any interesting post-game content, champion alder was a shit champion, oh and triple/rotation battles were lol.
B2/W2 holy shit was a huge improvement over B/W. Finally a sequel to a pokemon game that we hadn't has since G/S/C, great music still, many QoL improvements, introduced the Pokemon World Tournament which was fucking awesome! It brought back every gymleader/champion from every generation. Ghethis unfortunately went from an interesting villain to being a generic "i'm gonna take over the whole world/region" type. Aside from that I don't have too many criticisms regarding B2/W2. I wish since it was a sequel that you could meet and battle Hilda/Hilbert/White/Black from the previous game like you could with Red in G/S/C.
X/Y I really don't have much to say. Introduced Fairy typing which was interesting and some of the pokemon were pretty cute. Pokemon like Togekiss got a much needed type change which was great for competitive and good fuck over dragons. First mainline pokemon game to have fully animated 3D models which was also pretty huge and to add on top of it all, you had pokemon amie which to gamefreaks credit was pretty ambitious since every pokemon had their own custom reactions. Friend safari was an actual good addition and made ditto hunting for good IVs MUCH easier. Super training made getting into competitive battling much easier.. Megas were kind-of a hit or a miss but I personally loved them since some were really cool looking and my favorite steel type pokemon got one in Mega Mawhile! X/Y overall was pretty fucking mediocre though because it was too basic of a pokemon game compared to at bare minimum pokemon platinum. Non existent postgame, game was a bit handholdy, Diantha was an even shittier champion than Alder but atleast she's waifu I guess. Now one thing I did like about X/Y was how easy and fun it was to hatch shiny pokemon. Some mad lad created this program called instacheck which made getting a competitive shiny pokemon actually possible with patience. There was even a subreddit called shiny value exchange were with your Secret ID you could give an egg to a guy that had the SID that you needed and they could hatch you the shiny guranteed. It was all great until gamefreak had to be fucking faggots and updated the game to where the damn program didn't even fucking work anymore.
ORAS I didn't bother buying and I never will buy. Funny enough this is actually another reason why I fucking hate gamefreak now.. This pretty much explains it:
Gen VII as a whole I really didn't like all that much and hardly have all that much to say about it. Starters imo all looked like shit, alot of pokemon look lamed and were even worse in competitive. Like Gen VI, mythical pokemon weren't much of shit since they didn't have their own story events like Gen IV did.
EXTREMELY handholdly game, bland looking region and looked very unappealing, totem battles were to be fair interesting but execution really wasn't all that great and I'd rather have gym leaders back. There were somethings I liked about Gen VII though like Guzma, Lusamine, Aether foundation, and the fight against Professor Kukui but aside from all of that I can't say much else.
Gen VIII funny enough was actually better than gen Gen VII imho but even then thats not saying much. You did get some QoL improvements like being able to wonder trade without being stuck on a screen...a rant about this later. Raids at least kept the game somewhat fresh until people figured out the exploit where you could get whatever pokemon to spawn in the den aslong as you date skipped. Became even easier to get shiny pokemon thanks to seeding bots/websites. Story was a big nothing burger for the most part. I loved the gym battles though because they actually felt pretty huge. Game is still pretty handholdy and the region was once again boring even with the fucking low res wild area. Verlisify will still tell you Gen VIII is the best pokemon game ever and you're a hater if you say otherwise though. Oh and have I mentioned how this probably the most boring fucking pokemon game I've ever played? No post game unless you count that shitty DLC to be postgame and even then it should've been free. As far as #Dexit goes ill say this: If Gamefreak just said "Not all pokemon will be there at launch however, we plan on adding them back in future updates" that alone would've atleast mitigated the damage they got but instead they have to be retards and lie about their reasons for not adding them all.
So about wonder trading...they fucked up very hard with this. So some asshole during Pokemon Homes launch decided to send "malicious pokemon" that you would receive via wondertrade. This pokemon would stay in wonder trade and if you claimed it your fucking game would crash. I was one of the people who got this pokemon and I basically couldn't get online to do jackshit. Why you may ask? Because how you access the Y-comm is by litteraly pressing Y. When you get a pokemon via wonder trade you MUST press Y so you're locked out of ALL wifi communications because of this bullshit. Guess how long it took them to fix this issue? 3 months. Yeah you heard me right. 3 fucking months to fix this meanwhile theyre still churning out content updates while I and others can't even play the rest of what little the game even has to offer. Tbh I'm still kinda pissed about it.
The only pokemon games I'll buy now are probably just spinoffs. I'm not hopeful for an actual good D/P remake either seeing as how gamefreak has changed. Anyways thanks for reading my post if you even bothered lol.