Sorry this is so late in response. Shikamaru did meet Kurenai and her daughter. Naruto did meet Shikamaru before he left the village, but he was more of a pest in the novel. Shika was getting annoyed Naruto wouldn't break off after a while. The anime made it seem as if Naruto just brushed it off, wasn't suspicious, and left. In the novel, you knew Naruto was certain Shikamru was hiding something.
The Kakashi meeting Shikamaru with his coworker was filler. Them reading Sai's message was in the novel. The anime did leave out the grim tone the novel had. Kakashi was dead set on the assassination mission, but Shikamaru put his foot down and specifically stated that Naruto can't go on the mission, because killing someone would change who he is as a person and Naruto is destined to become Hokage. The novel does a good job of making it known Shikamaru is taking this mission to protect Sai, but also to protect Naruto from seeing the ugly side of the ninja world. Naruto at that point was still Mr. Let's talk things out.
Hope this helps. I can answer more question about the novel as the episodes air or as you have them. I've read all of them except the Naruto/Hinata Wedding one.
