What class/classes are your watchers? What kind of backgrounds did they come from? How'd they all feel about owning a keep and then losing it?
Wauliani (my main watcher, and the one I’ve played the most) is a Death Godlike monk. Tomas is a Hearth Orlan wizard. Petrella is a Wood Elf Druid. Axiti is a Wild Orlan Barbarian. Koami is a Coast Aumaua Paladin of St Elga
Wauliani is from Rautai, and she’s of aumaua descent. Her parents  abandoned her at an orphanage shortly after she was born, and she had a rough childhood, without much affection or support. She learned her monk skills from a old drifter who took a liking to her, and fled the orphanage as a young teenager. She’s not cruel, but she’s very straightforward and unbending.
Tomas was a slave in Aedyr. He escaped as a young man after his mother was sold, stealing a grimoire from his master which e used to teach himself reading and wizardry. He’s nervous and jumpy all the time, but he’s kindhearted, frequently to the point of taking too much on.
Petrella is a noble from Old Valia. She grew tired of the endless politicking and the constant talking of old glories and hopped the first ship to the Dryrwood. She’s plucky and energetic, and wants to be a good person, but she’s still affected by her super-priviledged and sheltered upbringing.
Axiti is a rebel from the Ixamitl plains. She lead an orlan revolt against an oppressive human landlord, but when the rebellion succeeded, they were betrayed by one of their human allies. She’s pretty angry, but understandably so.
Koami is also from Rautai. He was working as a blacksmith’s apprentice when his master died, and he spent time feeling purposeless before he found the Shieldbearers. He’s a pretty cheerful guy, but part of that is natural and part of that is because he’s desperate to be nice and be liked so he feels useful.
I can;t articulate everything, but I feel like Tomas at least was a little relieved because he kept being afraid he’d mess it up