When I rolled stats one of the numbers I rolled was a natural 20, i've never had that before but the character has no minus stats. I just want to be sure this is ok.
All of the characters should know each other, or at the very least have met before traveling to Greenest. Escorting supplies or perhaps a local businessman into the town would work. Could be as simple as having a character or two that live there and you're all stopping there after your latest adventure.
You're a Bard right? Perhaps I saw you perform at the local tavern and enjoyed your performance enough to hire you to accompany me and share your tales