Hi Liz! I'll admit, I have a soft spot for Sebastian's face, so any opportunity to use him in new games is a blessing (also - bless Lindsey).
Nick - They'll definitely get along, since Jackson is of the more friendly and optimistic variety himself.
Demi - Jackson enjoys a good bar so it's likely they will meet there if not beforehand!
Kitty - It's likely they will interact at some point, whether through the capitol or Maizie and company.
Bishop - Aside from his time in the military and any people with similar history, he will be the most familiar with biker types because he knew some back in Memphis. I've opted to not go the DoR route but it will still be interesting to see how he reacts to the Hellhounds and vice versa.
Sasha - Jackson might certainly be considering more tattoos now that Navy regulations aren't of the most importance to him in that regard!