1:09 PM
@NautArch Ok, that's cool, Monday night is a big of an odd ask if you have kids.
@V2Blast If you go with Bron, I am searching for an area that sort of fits your back story idea. It needs to have orc raids; the serial "live on the outskirts of town" theme puts Brons dad and mom in the "small claims farmer and herdsman" category of homestead. With dad being an Orc, the "raise cattle, goats, sheep, aurochs" back story as an orc fits pretty good. His whole focus in orc raiding parties was loot, stock improvement etc.
The unique meeting with Bron's mom is a cool bit "not likely, but this fits" and mom would be some kind of outlander or pastoral background herself. Not liking "society and its constraints" gives her story a bit of "so we headed west to be free and to not be too near to the neighbors" feel to it.
So Bron is raised on a homestead not far from a small trading post or hamlet; not a town, nothing so grand. I am looking at Ulek, Principality, eaastern region. That would put them in an area that is with some frequency subject to cross border raids from the Pomarj/Orcish EMpire zone in World of Greyhawk.
Also, the "school" scenario would be seasonal, not the way you and I grew up in a school. During winter or summer there would be a few months of book learning for the local kids, but during spring and harvest they are all out working the land with mom and dad. But it still fits into your overall pattern of "not quite fitting in"
And living off the land, etc.
There's a river nearby that has a port city, and that's where Bron eventually finds a good fit on the Lady Fortune.
Anyway, that's what I came up with after your summary and looking at the map. With the long service on Lady Fortune, Bron will have stopped into Saltmarsh at least once in the past, so Ican figure out at least one local NPC that Bron knows of, or had an encounter with. Current idea is the halfling merchant WInston, will talk with you more later on when I can be on discord.