LFG/LFD/LFR and the introduction of cross realm zones and server mergers. I personally feel like my worst time in this game was the downfall of community when everybody had the chance to be anonymous and to be a jerk. Before all of this, people actually had to group up and be responsible for their actions. Otherwise they were forced to either faction change or server change.
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MS warrior and 29s+ rogue stunlocks. Not a fan? =p
“Carp, the rogue’s in full T2!”
Those were the days.
Also, a lot of classes just felt uncooked. Shaman has always called to me, and it’s one such class that didn’t feel complete until Wrath, frankly.
When I stopped playing before WoD launched. I had no interest whatsoever in more orc nonsense.
But as time went on. I missed my friends and posting here. The reception when I came back midway thru Legion was at least sweet. Very “Jack’s okay!”
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Early MoP literally destroyed all the networking I did until then, like 80% on my btag just wen’t grey forever and I just didn’t feel like going through the hassle of multiple lfg fails again.
MoP completely changed combat, every1 I knew quit for how wacky pvp got.
Shaman tended to be hit and miss, but pretty loud in one direction or another. A lot of complaints about windfury one shots.
I found warriors more fun to play against. They were fun to root. And then root. And then root again. And then root once more. And then apply one round of moonkin dancing. And then root again. The important part was the moonkin dancing though, for obvious reasons.
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My worst time was 11.0 when blizz decided to destroy the mage class by deleting the arcane momentum talent that gave us that speed boost. It was the only talent holding that class together for me, so I had to ditch it permanently.
Firelands and Dragon Soul. I’d learned to raid in Wrath after a friend got me into WoW and the first tier of Cataclysm was my first big progression tier. It was brutal and I loved it to death. Then t12-13 were so, so miserable.
Except the worst fight of the whole expansion. Spine of Deathwing was quite awful but every class had an extremely hyper-specific optimization strat for it and executing on that well was kind of unique and immensely satisfying.
I only played the launch patch of SL so I dodged SOD.
Despite being two questlines away from loremaster, Shadowlands. Just Everything about shadowlands, hated the entire expansion top to bottom, and it killed wow enough for me to completely skip dragonflight.
I’ve had moments I hated like the killing Cairne off screen thing or the like but the only time I can honestly say i hated the game was Shadowlands. All the stuff that made sense before they took a match to and blamed the jailer for it all and the jailer was a total wuss and badly written guy. They defiled Sylvanas’s story by being associated with the guy then threw her in the trash. I ended up taking a break sometime after sanctum dropped and Sylvanas was made a raid boss after years of them promising she’d never be one. Then also gave her a legendary which motivated people to farm her… Baine sickened me as well…it was a very bad time. I didn’t come back from that break till a few weeks before DF hit but I still want to BBQ Baine over a fire, more so after DF and his cry baby tantrum and alienating the centaur I bust my tail trying to be friends with (despite all the centaur trying to hook me up with their kin when I’m uh…yeah no thanks I’m good)
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I would also say Shadowlands, since it was the first expansion where I felt my paladin was not viable in content I wanted to do (M+) and I swapped to my hunter because it was so much easier to get into keystone groups.
For all the bashing of the storyline I see… I thought SL itself was ok (not a Legion by any means, but still fine for what it was… Sylvie got done wrong but that apparently was an IRL bad writer with a misogynist axe to grind that went unchecked by management).
The death of Nathanos and the Sylvanas “soul healing” arc in Shadowlands. I’m still angry and grieving.
Wod.
The massive content droughts and being secluded in your garrison just felt awful.
Definitely the loneliest xpac to date and the one and only time I ever took a break from wow from utter demoralization to play.
Right now. Sitting and waiting for Bloodbrine to spawn in the new Korthia. Much fun much WoW. Reminds me of the Scourge ‘event’ where we stood like trees for half an hour for a chance on a 30 slot bags. 
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End of vanilla/beginning of BC. The company I was working for relocated out of state and I couldn’t move with them. Spent a year doing BS odd jobs before being able to sell our house and move back North. Was a very stressful time.
As a result I can’t go to any zone in Outland w/o thinking about how much that sucked.
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Shadowlands, my guild fell apart, I became a drunken mess. It’s not the expansions fault. Still, worst time for me!
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Shadowlands was a complete bust for me, not for personal reasons, just hated it. Going back to do some farming, there are some high points, but yeah a lot of just blah for me.
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ALL of SL’s.
The only redeeming quality SL had was Revendreth as a city/castle was awesome to look at.
other than that…
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Same. Seeing multiple guilds report that they got no loot when clearing the first raid after it opened. That and the multi month rep grind, Idgaf that they slapped a sticker on it that said “Renown”, to unlock flying caused me to quit for years. I only came back for the Mists of Pandaria: Remix to see if the expac was as good as I remembered or if I was full of nostalgia and rose colored bs. It was the former, btw.
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Was it the bridges? Bet you it was thralls earth bridges.