I try very hard to not open this box of memories, just cause it would take soo long and it would make me super emotional. Here are the ones I can think of within a few minutes (edit: nvm, I spent way too long on it):
Not being able to log in due to server cap
Crashes and lost/rerolled Pokemon ( I had a MS word doc where I carefully arranged the screenshots of all my Pokemon and their IDs in case I got hacked or something lol
All the old forums
IRC! So clean, so fun. Playing uno with mates like LunaticJames, Pansy, Naero etc.
Guilds <3 The real, active ones and all the fun we had
Rare Hunters vs CrypticComplexity - two biggest rival guilds that everyone wanted to be in.
A small place near that Leaf Gym City (Celadon, Cerulean, idk really), where we could race our friends on bike or surf and win tickets.
A couple of drama topics:
The huge Shane fight lol. I hope no staff is salty about it still.
Remember when that Christmas gifter - SethShadows turned out to be a huge scammer?
Slim/RoadHouse - an amazing/weird friend turned out to be a big hacker lol. There was some drama around that too
Speaking of scammers, BR Hackers! God they were annoying and ruined the game, but damn did Fonty and the Ban Hammer Bis do their best to shut them down. Those Ban Appeals were fun to read. (I went to get milk man, my brother must've done it!?!")
The huge auction hosted by the staff.
The levelling up and "explode/SD" to quickly level up. I was still too lazy and underpaid Fadoka to level up my pokes.
EVENTS are by far the happiest memories I have made in the game. And quite honestly, I still smile when I think about them. Please someone tell me if they remember that huge Halloween event where spitiomb was released. It was a cave then a huge maze that started from Ecruteak. Those few days I still remember after 6-8 years - that's how good that event was.
Some Christmas events were great too
The first Chinese New year event was amazing as well - one of the most uniquely new and successful events ever carried out in PWO.
The people! Everyone was a character.
HOLY HELL the old WIKI!! Anyone remembers that?? iblamelee.co.uk was where I've spent several hundred hours editing stuff and updating for absolutely NO GAIN. It was so pointless yet I worked very harsh with it. I hope everyone appreciates that. Naero or HitmonFonty also worked on that a lot.
Mapmaking was fun (and tiresome), for the select few who have tried it.
The entire "signature making" business was cool. Artists really had a place in PWO and were respected. I remember rbecca and Olman to name a few.
The in game trading portal / auction house in Pokemarts!! I really hope some people remember this because it was something very special. There was no other mechanism to trade back then without being in a pokecenter with the same person at the same time. There used to be lists of pokemon and their prices. There was a genuine THRILL attached to auctions then. You could even snag some 1 Pokedollar mons if you were lucky lol
The Water Lab!! It was in Saffron City and had dratinis in it. Just a very small map where people spent their entire lives. The safari zones, splitting river reserve and (later) Dragons Den were nothing compared to it lol.
I really don't want to spend more time thinking haha. I'll update this if I do remember something else