This chapter is at the beginning of volume 2 of the LN, and we still have many chapters before Olivia's drama gets resolved at the end of volume 2.  The manga screwed up a major source of Leon's and everyone else's character development since it cut out much of the fighting with the sky pirates.  I believe that Cara's family is within that bitch earl's daughter's territory, so they have to follow whatever they say.
In the LN, the sky pirates were a much bigger threat and almost took Olivia hostage when she stupidly rush on deck to try and do something.  If it weren't for the two idiots (forgot names), Olivia would've been captured and Leon would've had to surrender to save Olivia's life.  Seeing Leon single handedly overpower the sky pirates frustrated the two idiots into realizing just how immature and useless they really are, and come to admire Leon as a result.  They get their chance to do something when Olivia is in danger and nearly die saving her.  Leon sees this and realizes that one of the major reasons for Olivia feeling depressed is that Leon and Angelica have been stealing all her character development.  By protecting her all this time, Olivia was never able to grow into a stronger person.  Justifiably worried about how Olivia would be able to be strong enough to fight the big boss in the future war, Leon starts distancing himself a bit from Olivia.  It isn't until the first major battle at the start of the war that Olivia surprises Leon by stepping up to save everyone and yelling at Leon to finally see her as a woman instead of a game heroine.
Angelica has her own drama about coming to terms with who she is now and how she used to be before finally making up with Olivia in the same volume.  Volume 3 is about the war and the two girls literally having to corner and force Leon into marrying them, because he's too much of a coward to actually do anything.
Volumes 4,5,6 are about the second game that Leon didn't know about (since he died before it was released) and takes place in a completely different nation called the Azler Commonwealth.  Marie is essentially a completely different person that's really likeable and really would be the best girl for Leon if they didn't believe they were siblings in their past life (the Maire SS route has them believe otherwise and they get engaged; it's arguably better than the main story).  It also introduces the most infuriating, sociolpathic bitch that Leon can never get rid of because she's the second game's heroine's sister.  She's basically the story's herpes in that she's the cause of all the problems and keeps coming back to cause even more problems.  Literally every comment about her on reddit is about how stupid she is and how much people really hate her lol