How many was the most times you ever grinded an instance for a single specific item?

[Rasylia]

Around 500 or more runs through Brayflox HM to get the Opo-Opo. I ran with newbies mainly and geared up at least 4-5 of them, had nice talks, explained things, brainstormed about crafting [...]
Good old days.

[Chimeric]

From about 2.05 or so to over halfway through Heavensward, it took roughly 3 and a half years to finally see the Ancient Sword in Stone Vigil and win a roll on it. Leveled almost every combat job to 60 before I managed to get it on an unsynced run.

[Kyrph]

I been soloing Odin for maybe 20+ times not to get the full DoW set but he will not drop the pants of the set. So probably going to be 30+ T_T.

[Freyt]

I did Ramuh Extreme like 20 times trying to get the scholar book way back when.

[Korihu]

Hmm, I wasn't specifically farming for the item since I don't really care about minions, but I don't think I got a fenrir pup until I completed around 300-400 Feast matches.

About 600 runs of Garuda to get Nightmare. (Got all three tank mounts from that fight haha, I guess the number would be a bit higher for the times I farmed Titan and Ifrit for their horses too)

And about 50 runs of a specific expert roulette, can't remember which, for some glamour item somewhere around 3.3.

Outside of those though I've had pretty good luck in general for most stuff.

[Cemil]

Think 5 Months camping for Eurytos Bow.

[Serilda]

I spent the better part of a year running Toto-Rak for the cool superhero-style mask. Thank goodness for undersized parties. The worst thing is that it's undyeable and DoW-only so I can't even use it for as many glamours as I'd like (the only alternative which looks similar is a horrible colour, so I had to suck it up and farm the black one). It just would not drop!

For pets and music I'll always just buy them if possible, it's not worth the pain.

[ChloeGrace]

Halatali hard mode 112 times for that stupid dungeon atma.

[Claire_Pendragon]

Back when World of Darkness was new, I used to run that for the Tank body piece. (lowest drop rate for the items there)
After half a year, still didnt have it, and HW was comming out, and the already long tank queues skyrocketed up to 4-6 hour queues.
Then void ark came out, and queues were over 12 hours long.
Then relic came out, and queues dropped to 45-60mins, back to 2.5 times.
Then one day I went healer, wanting the healing skirt, and messing around, of course it dropped, and the tank already had it, thought id get it. Nope, tank hits NEED, because he wanted to desynth it. As his armor is on his retainer, so he could get it again, and what he's wearing is just a glamour.
Sometime in 3.4 I managed to finally get it. (I didnt queue up for it as much in 3.4, as I started raiding again.)

As for the number of times, no idea.
W/O doing ANY quests, dungeons/roulettes, ANYTHING, and doing JUST WoD, I got my PLD from 50 to 60, and my WAR from 50 to 57. (I actually ran this on my alt as well, got her from 50 to 60 on this as well.)
and did it as DRK on and off, and after hitting max.

Drop rate of that thing is ridiculously low, and even more so for a role thats already impossible to get into 24man content with.
But MNK? before SAm was a thing, of course it had the highest drop rate, despite being one of the least played jobs, and other jobs shared the same gear, like Casters, and Healers...

[Lord_Zlatan]

Im beginning to really hate Saint Mociannes Arboretum. Been soloing it on RDM for the stupid Plague Bringer's coat to complete my Sorin Markov/Sadistic Vampire RDM look. I got the boots and the gloves on the first run... not looking like I'm ever going to get this stupid body. The silver lining is that its easy to solo, taking about 20 minutes per.