Alright, I'm going to throw the unpopular opinion into the ring here, but I'll start with a disclaimer- I was not an active raider until Secrets of Faydwer expansion. By then they had removed the key requirements for both PoP and OoW, and I experienced both of those expansions from the point of view of a 75-80 character who mostly solo'ed and duo'ed the camps of interest in those expansions, and went on maybe one Time Raid and a handful of Anguish raids.
I had the most fun in OoW. Yes, GoD was a dumpster fire, and the only time I spent there (was active through House of Thule) was for AC aug camps as necessary for my SK. But OoW was super fun. Epic 1.5/2.0 was a much-needed addition to the game after Velious rendered some epics obsolete, the Anguish armor was very impressive and the chests had unique clickies, and the other gear still felt unique.
Wall of Slaughter, the 65-70 exp zone of choice, was a zone that kicked you in the teeth when you came in unprepared. Even Dranik's Scar, the 55+ entry zone for the expansion, was very hard for the new players coming in. The series of trials in Muramite Proving Grounds that permanently increased your character's resistance caps was a unique addition, and the Pyrilens especially looked awesome.
Then there's Anguish. I can't deny the awesomeness that was Plane of Time (I ran through the script a few times in Imperium Server and agree it was about as epic as it comes), but Anguish just felt more fun to me. Especially because people would walk away from there with orbs for their 2.0's. The boss gimmicks were very fun, including having to collect the masks throughout the zone to beat OMM's gimmick at the end.
After OoW I literally don't remember the expansion order. Serpent's Spine was actually fun since it gave newbies new areas to play in, and Seeds of Destruction was ALSO extremely fun because of the time travel aspect- nothing beat going back to the Field of Bone before it was the Field of Bone and talking to Trakanon and Jaled'Dar as quest NPC's, or exploring Qeynos Hills as humans had only just landed there and called it Oceangreen Hills/Village. The deep dive into Kunark lore especially kept me interested.
PoP was cool, and it was awesome getting to meet and in some cases kill the Gods you picked at character select and only read about, but I have to say OoW just did it for me better, with Seeds of Destruction a close second. The experience declined for some expansions but was better in others, and I think we were just spoiled by the consistent quality of classic-kunark-velious and PoP.
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