The Pirate Hoop  

I just got this today from one of the nerius pirate type mobs today (cant remember which type though sorry - ie. may have been a nerius pirate, a nerius seer, a nerius dockhand - I dont know), so yes its does still drop.

And Obere only spawns as part of one of the freeport armour quests so thats probably why you couldnt find him (its one of the chain quests I believe - though again I cant quite remember - I wasnt doing it).

I was able to finish this quest as a Qeynos player. You have to go through The Scrawl and into the Theives Way to get to Beggar's Court. I didn't have to go through N. Freeport. The merchant is on top. There is a Captain and guard you must avoid.

talked to the NPC merchant in North Freeport, she told me to look for Sympronian in beggar's. I went to Sympronian, and he won't respond to my hails. I'm a 26 SK... guess he doesnt like trolls?

This NOT doable by Qeynos players. You can get the quest but the merchant will not respond to hails. Getting by the 2 guards was a pain in butt to find that out.

Your from qeynos? bummer...