I haven't played Platinum yet as I normally don't get the 3rd game of a generation. About the discussion of the best generation, it really comes down to preferences and which aspects of the game you hold most close to your heart. I for example don't give a d@mn about the night/day feature. It's neat, but I can sometimes get tired of seeing night time graphics from wanting to only play video games at night. Well, without further explanation:
Red / Blue / Yellow
Positives
+ The first game. So credit for the existence of Pokemon goes to these games
+ The 1st generation Pokemon were heavily based on worldly things such as various animals and plants, and it wasn't difficult to tell what they were based off of. Many of the later generations have pokemon that are difficult to tell what they are based off of and some pokemon are just cool spiky things. This can't be argued as a positive for everyone's case but it is a common thing people like.
+ THE ATTITUDE - This generation really put more contrast between trainers who treated their pokemon well and trainers who did not than any other generation. The only game that comes close is GSC. Unlike what you see in RSE and DPP, in RBY, most trainers didn't treat their pokemon with love. In fact, many trainers had whips (even the Gym Leader Sabrina). In this story, it was the job of the main character to learn that loving his pokemon wielded the best results despite what the rest of the world thinks. Trainers in general also had a darker tone. Most of the trainers didn't look friendly at all, especially the gym leaders and the Elite Four. I could even go on as to say that the pokemon were more vicious looking here than any other generation.
+ Appropriate number of legendaries. Really the point of legendaries was that they were rare, hard to find, and really powerful. Mewtwo was meant to be one of kind and the most powerful pokemon in existence, but now there is also Lugia, Ho-oh, Kyogre, Groudon, Rayquaza, Deoxys, Dialga, Palkia, Giratina, and Darkrai.
+ The difficulty was decent. It was possible to get stuck a few times, but it wasn't impossible to get unstuck either. Usually, just some good training against other trainers and wild pokemon could help.
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-+ This game is really glitchy. Some people disliked that fact, while others loved it and enjoyed playing with Missingno.
Negatives
- Bad graphics. Despite having a dark tone, a lot of sprites looked really bad. This doesn't apply to yellow as much as Red / Blue / Green.
- Bad music. The note charts weren't bad, it was the sound quality used. Very old and outdated
- Small region. This generation has the smallest area to explore out of all the games. Compared to RSE and DPP, the towns and roads were really small and cramped.
- Dumb *** AI. Omg Agatha, stop using Dream Eater with Gengar, I'm not even asleep! The wild pokemon were okay, but the trainers were not any smarter and simply picked random moves.
- Competitively imbalanced. Trap moves immobilizes opponents and boils down to luck if the wrap pokemon is fast. Psychic type was without a doubt the best type in the game, being unaffected by Ghost and having no weakness except to the weak attack, Twin Needle. The number off pokemon that were commonly used competitively is really small. Double Team and sleep is God broken, even though they are too powerful in all generations. Special Stat covers both offense and defense. Everything largely boils down to type trumping.
Gold / Silver / Crystal
Positivies
+ Night / Day. Now the game has an internal clock that keeps up with the day of the week and time of day. Events and pokemon appearances could very depending on this. While this was mostly fun and created more involvement, this sometimes backfired on people who had time restraints and could only play pokemon at certain times.
+ Male / Female and Breeding. This was a cool feature that has been a staple since. What's not to like about it?
+ Revisit Kanto. This is still the only generation to allow you to revisit another region. This was really cool for nostalgic purposes and it was great to face all the old trainers. I was kind of dissappointed at how quickly this region was to beat.
+ better AI. Players weren't extremely stupid anymore.
+ Better graphics. Instead of having black and white or shades of a single color, GSC had multiple colors. The grass was green, the pokeballs where red, the houses and different colored roofs and you were orange!
+ Special Split. Now there is SAtk and SDef!
+ Love / hate. Added a new way to evolve your pokemon as well as provided two new moves.
+ Better competitive metagame. They changed the trap moves and added plenty of new moves such as spikes, protect, and roar to add to the game. With breeding, you could create diverse movesets for your pokemon. They also introduced holding items and two new types of pokemon.
+ Really good sidequests. RBY really only had 4 legendaries and a few people to find with items as their sidequest, while in GSC, catching the 5 legendaries was more involving, and you could go exploring in all the extra caves and people were harder to find.
Negatives
- Easy. I know I just said that they had better AI, but their pokemon were so weak that my pokemon eventually became stronger than whoever I was facing by many levels, which never happens in any other generation. More specifically, the opponents stop growing stronger for a while after you beat Jasmine, and the trainers in Kanto all use level 40-50 (with the exception of Red and Blue).
- The pokemon have the least menacing look in this generation. Everyone looks like a shiny plush doll, including Charizard and Gyarados.
- Competition wise, while it was deeper in strategy than RBY, it was also known for epically long stall wars. 2 player matches take forever here.
- Did the music get better? Barely
- Slow HP bars. I believe this generation was the game that started the bad trend of watching HP deplete really slowly at high levels.
Ruby / Saphire / Emerald
Positives
+ Best Graphics. This generation arguably has the best graphics of all the generations. Scenery is really beautiful and the battle fields were great too.
+ Great music. The songs on here were always fun to listen to and it really stuck out after hearing RBY and GSC sounds for years. The Elite Four having their own theme was really bad *** too. The RSE pokemon sounded good as well.
+ Huge Region. Most players do not realize this, but Hoenn is actually larger than Johto and Kanto combined! The towns and cities here were enormous and beautiful as well as the routes.
+ Fastest movement. You can run on foot now and you get a bike that is extremely fast. You were going to need this too to explore the huge region!
+ Competitive overhaul. They added EV training, Natures, even more moves, really crazy items, and pokemon abilities. All together, it dramatically changed the game.
+ Double Battles. Now you can send out two pokemon at a time or do 4 player 2vs2 teams.
+ Pokemon Contests. Not the best new feature, but was entertaining
+ Battle Frontier. For lots of replay goodness.
+ Intelligent AI. DPP and RSE both share about the same level of AI, both fantastic compared to GSC and RBY. The NPC in this game also tend to use a bunch of items increasing the challenge.
Negatives
- No Day / Night. A feature that was unnecessary to remove but was removed anyways.
- Couldn't trade back with RBY or GSC (this was due to the competitive overhaul)
- Lacks the darker tone that RBY and GSC had. Team Aqua and Magma weren't as sinister as Team Rocket.
- Lack of a good rival. I really disliked the loss of a that snickery, "Hey I'm better than you!" rival. The rival even gives up on training before he/she fully evolves her starter!
- Weird pokemon. This is where they began doing things like having pokemon with spikes and odd designs on their bodies.
Fire Red / Leaf Green
Basically RBY with RSE's competitive overhaul, graphics, and music. They did take away the dark tone though.
Diamond / Pearl / Platinum
Positives
+ Zomg pseudo 3D!!!
+ Best pokemon sprites. RSE may have had the best graphics overall They introduced varying difference between Male and Female which was really cool.
+ Online play. Who can argue with being able to play and chat with your friends over Wifi? That's really nice.
+ World Wide trade.
+ Physical / Special Split. Added some realness because of the oddness of having moves like Shadow ball and hyperbeam be considered a physical attack.
+ Overhauled Pokemon Contests.
+ Even more Competivie goodies. More moves, pokemon, abilities, items etc.
+ Online battle tower + new Battle Frontier.
+ Best difficulty. The levels are high AND the AI is intelligent.
Negatives
- Slowest attack animations. So slow that I had to turn them off.
- The extreme levels of offense makes defensive tactics worse than before. Not a terrible thing though.
- Weird pokemon. The weird pokemon with spikes continue.
- Too many legendaries. Way too man legendaries.