So, for me Pokémon is all about favorites and opinions, and, more importantly discussing those opinions/favorites to see who has the best arguments for their opinion! Or just to see what everyone´s opinon is. That´s cool and interesting too.
These ´discussions´ can concern everything, from Pokémondesigns, generations, card-artworks, or, in this case, your favorite (or best) set per generation. Arguments for why you think this is the ranking are very welcome but just ranking is ok too (the arguments make the post pretty long I found haha). It will be interesting to see if there is some consensus.
For me it wasn´t a very long think. I had the most trouble with XY because there isn´t a clear ´good set´ in there. They all have problems/strengths (well, most). So, here goes.
Gen 1; Base set, Fossil, Gym Challenge. Base set is just too nostalgic to not be first. The Venusaur, Charizard and Blastoise are just pure joy. Fossil was the set with the first Lapras card and I also just enjoy the artworks. Gym Challenge is the ´strongest´ set in this block I think with beautiful artworks/selection.
Gen 2; Neo Destiny, Neo Discovery, Skyridge. Neo Destiny is my favorite set in all gens. Just class with the Dark/Light/Shining types. Neo Discovery has the best theme (and pack/box artwork) with some beautiful cards as well. Skyridge has that legendary status for being the last, short-printed WotC set.
Gen 3; EX Unseen Forces, EX Dragon Frontiers, EX Dragon. I´m gonna be honest here, I didn´t collect/invest during gen 3 (or 4) and when I got into it again these sets weren´t as interesting to me, and later too expensive. As a result i don´t have strong opinions, but I do really like Unseen Forces.
Gen 4; Stormfront, Majestic Dawn, Secret Wonders. This, for me, is the weakest era in Pokémon. The sets kind of blend together. That being said, there are a few winners. Stormfront is underrated I think and sets like Secret Wonders are so elusive that they create their own mystery.
Gen 5; Dragons Exalted, Plasma Storm, Legendary Treasures. The secret rare Rayquaza elevates Dragons Exalted to first place for me. Also a strong theme. Plasma Storm is just a really strong set and Legendary Treasures reminds me of Evolutions. It is fun.
Gen 6; Phantom Forces, Furious Fists, FlashFire. This is the gen that got my second Pokémon life to start. That does mean that nostalgia plays a part in the ranking. Phantom Forces has a strong theme, and some strong chase cards. Furious Fists is a very unforgiving set (I have seen someone pulling 1 Ultra Rare from a box. 1… But, I am a Lucario fan. FlashFire is a frustrating set to open, however, pulling that M Charizard X is the closest thing I got to pulling Base Set Charizard.
Gen 7; Unbroken Bonds, Team-Up, Cosmic Eclipse. This one was the easiest for me. The Tag Team sets just were so much better than anything else here. Unbroken Bonds is very underrated if you ask me, Team-Up underprinted which gives it an extra, and Cosmic Eclipse is a really solid set and more fun to open with the gallery (not that you would be opening these anymore, but still).
Gen 8; Evolvins Skies, Lost Origin, Chilling Reign. What to say about Evolvind Skies. This set has it all and is my second choice for best set overall (after Neo Desiny). Solid chase cards, a generation definining card (the Umbreon) and a beautiful box. Lost Origin has a really strong theme and Chilling Reign just has a lot and may have been a bit overlookd and thus underprinted (not that that was really a thing anymore during this era).
Gen 9 (so far). 151, Paldea Evolved, Surging Sparks. Gen 9 had only just begun when the third best set came along (151). Solid chase cards, fun to open, a lot of good artworks. Paldea Evolved is really strong for a second set (the Magikarp). Also fun to open. Surging Sparks has not been released yet, but I think it will be better than the ´Paradox Pokémon´ sets. A honorable mention for Obsidian Flames which is a Charizard set with a beautiful chase card.