[@Sigil][@Lady Amalthea] Tagging you two as per your request. :)

Kristina Smith
Jobs: Kristina I think will be better off still working out with livestock as well as agriculture maybe work in the medical garden from time to time with Niesha just to keep a closer eye on her after what happened to Sophia, and possibly given more responsibility out in the fields.
Skills: I can see Kris possibly learning first aid or some skills in the medical garden. 

Raymond Mendoza
Jobs: For Raymond due to his injury now that he is a one legged man lol. I could see him doing more along the lines of domestic maybe helping out with Meg and Ms. Sally with things there. If during the timeskip someone finds a prosthetic leg out on a run maybe working out in the crops. 
Skills: I'm thinking he will learn first aid due to him being in the infirmary for a long time during his recovery, maybe learning some French from good ol' Froggy as well.

Meghna Kumar
Jobs: I see her still doing the same jobs as domestic lead, not really sure what else she could do but she could take another job if needed.
Skills: Skills i'm honestly really not sure what she could have learned from the time jump.

Riley Ridgeway
Jobs: Riley for her I could see her being a recruiter due to her job before the outbreak, some people may recognize her from that, also going out on runs I could see her doing scavenging runs. I could also see her possibly training others kickboxing and Brazilian jujitsu.
Skills: Skills I could probably see her learning something from engineering skills.