He needs a vector in to the Veiled Hand (and the Queen's confidence). But he does not need to have been one of the attendants. "The Veiled Hand" generally refers to the network of information passed between attendants and friendlies.
But this is a new thing.
There's a surly kind of Queen's Guard named Menkliia who is the Queen's left hand on this. He's the highest up the chain that the PCs are aware of. Your handler is Stefen, "the pock-marked man" (echoes of the Farseer Trilogy is on purpose)..
Druvir is a prosperous port city in a fairly prosperous nation.
I acknowledge that the very fact that it's a port city means there must be other lands, other peoples out there, which we haven't defined. So, it
could be a thing that Oswald is from outside Aroen (the known land). Queen Jia appears to have a bit of a thing for collecting anomalies. I mean, she's got a Khunic Oathsworn among her court... (a dread figure from Khune, one of our current PCs).
So, to start off with, you'll want to decide what kind of land Oswald comes from.
- Kumlar, our default. A Bard/Troubador. etc would surely have a place. (A PC, Nathan, is Kumlaren).
- Khune, a Harsh land to the Southwest. More Arabic and Middle Eastern in influence (a PC, Cara Yisil, the Oathsworn, is Khundari)
- The Plains of Taren. Think North American Indian plains culture... (a PC, Arui, is Tarenti )
- Khadid, Once a proud nation, the land itself was torn asunder by the great magical working called the forbidding, which ended the Great War. The land exists, but it is corrupted and rife with twisted monsters and other oddities... But man is a hearty creature and there are scattered villages all throughout Khadid, still.
Several generations after the Great War, the Khadiden are multi-generational refugees largely integrated into their respective societies. But, it's sort of like the Medieval Jew in that tehy're a part of, yet curiosly distinct from their socieities, and probably often persecuted (or depending on how different they are, perhaps fetishized)... At the moment, no current PC is Khadiden. - The Cyrenni, Fisherman and pirates. The original inhabitants of Sachs Isl and the other Eastern Islands. They're not really defined beyond "fishermen and pirates, and the fact that Cyren is the second largest population center in Kumlar, and essentially the gatewway to the rest of the world. I'd probably rip stuff off from Freeport for that one. It's a blank whiteboard for you, if you want this...
Now, as to Skills... I see Lore and Rapport being predominant.
Lore
For being literate, learning your stories and songs, understanding the context of said stories.
Rapport
For making people like you. This is the performance skill, definitely.
Are you a all Familiar with the Lynn Flewelling's trilogY "The Nightrunner" series? It starts with "Luck in the Shadows". MY roommate and I refer to it as "the Gay Elf books" (because the main character eventually discovers that he's both, though not at the same time). One of the central characters (the main/characters mentor/lover is first seen as a a troubadour/bard type. And it's absolutely <U>perfect</I> for explaining why someone might criss-cross the nation, know all sorts of people, all sorts of things and be remarkably well-informed about the state of affairs all over.
This is just what I was sort of envisioning when you pitched the concept.
With that in mind, it makes the character less about the performance (oh, the rapport should be up there), and way more about the background... A bard absolutely must be talking to people, learning things... asking questions and possibly ruffling feathers in the process. That's how they get their stories!. And boy does that fit the into this game-concept really really well...