It took me 3 years to get that.
The helm socket from the isle of thunder in mop ,took me a month of continually dying to get through that forge but I did it !
Sandstone drake is another 3yrs on digging oh i hope never go through that again.
Decent looking mail for a BE Female…
A slot machine isn’t hard
Going through rote questing isn’t hard
More a consumption of time and tolerance for a badly designed grind
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I got the T3 belt and shoulders from Naxx 1.0.
And because I refused to pay tons and tons of money against people that were just driving up the price, it took until the middle of BfA before I could finally complete my T3 set.
What’s that… 14 years???
Absolutely one of the most ICONIC sets of gear ever put in the game.
And although I don’t want to see it “redone” as a T29 sort of treatment, I think I’d rather the T3 set itself have some sort of toggle to allow the user to choose between the old low-rez, and a new hi-rez texture. As iconic as it is, there’s no denying how dated it looks.
I’ve never been great with gold so getting fancy items was always a big deal for me
In cata i was poor as all heck but I really wanted to be a paladin (i was a frost dk main) so i saved up to buy purified legplates of evil (bis intellect plate pants from dragonsoul) because it was the non tier lookalike of the paladin tier and wore those for the rest of the expansion 
Then in wod my friend and i two manned every cata raid and below every week on multiple characters for months to get the gold to each buy a swift spectral tiger (600k at the time)
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Dignity from PVP
Its a tie between Rusty Mechanocrawler and Silent Glider. (From Arachnoid Harvester and Soundless)
Scythe of the Unmaker in the colour I wanted.
Finishing “Long Strange Trip” and getting the violet proto drake is probably it for me. Started in late Wrath, and didn’t finally finish until WoD. Got held up at least 2 years just trying to get the last couple of bits for the children’s week pvp achieve. People were being major a-holes to anyone who had an orphan out.
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For my first character it was buying the ability to use flying mounts. Back then I was short on gold. I would see people flying around. And I yearned for the ability to do the same. Once I reached the level to be able to buy the ability I realized I did not have the gold. So I did every thing I could to get gold until I had enough. It took some time but the day came I got a flying mount. Pilot License obtained.
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Back in 2009, the Gurubashi arena trinket, twice on a level 29 alt. Then 8 years later, dusting off that same alt to get the heirloom trinket. This was all done without fighting anyone, if anyone else was visibly present I stayed put. But I did get ambushed by stealthers many times.
Similar situation for the Darkmoon arena heirloom trinket back in 2018, but I did that with max level alt
waves her bow Because no one could help.
That sword that drops in Icecrown and possibly that enchant from Visions that makes your weapon shadow.
My will to live, which I recently lost again.
Holy Priest staff mage tower cosmetic was REALLY hard for me hahaha. That scenario was nuts.
Headless horseman mount. Started trying in 2008. Generally did the event every day on 10 characters. Got it in 2021. I screamed.
My friends & family probably also screamed, but mostly out of relief they don’t have to listen to me complaining about it every single Halloween.
I’m an atrocious PvPer, so getting the fancy Plate armor for my Paladin in BfA was probably the hardest for me to get.
I got to start the shadowmourne ql when current.
Wasnt able to finish until i came back in legion after quitting end of wrath.
Felt super epic then to get the base axe even.