The nature of the Kenny/Jane flashbacks. How it should have been handled.
I know some people who have heard the news are probably getting a little tired of hearing on how the flashbacks were handled but hear me out.
Yes, the way the Kenny/Jane flashbacks were handled was a lazy copout not in a way in which they were inconsistent with the characters but more so in a way that they were poorly directed and lacked a lot of gravitas and felt like a slapped together sequence created by a rookie intern at Telltale.
I can see Telltale's thought process with the flashbacks as they have to culminate in leading Clem to joining the New Frontier and how she leaves them and that's fine but here's how I would have done it with both Kenny and Jane:
Goal in Flashbacks: You have go to Wellington because that's where the New Frontier originates but the journey is different depending on who you are with.
(Kenny) 1st Flashback
It's been a few months, Clem and Kenny bond with Kenny teaching her new stuff, decent character development established here and there, then Kenny suggests on going to Wellington since it's been a few months and maybe Wellington will let them both in with AJ. There's a choice to go to Wellington or not, if you say no, Kenny will understand and if you say yes, Kenny will agree but either option will lead you to go to Wellington anyway since it's Telltale.
END
(Kenny) 2nd Flashback
Same exact setup of being surrounded by walkers and running into a New Frontier member except this time with Kenny. You're in the shelter thing and Kenny mentions they're running extremely low on supplies and Kenny feels that he and Clem should go to Wellington. You run into New Frontier member; Kenny does not trust her yadda yadda dialogue, she states that Kenny and Clem are viable survivors for New Frontier. Kenny tells her to back off a little bit since he doesn't trust her and mentions to Clem that they're running low on supplies and should head to Wellington and the New Frontier member mentions that she came from Wellington and is heading back over there, Kenny then says a line, "What?" the member nods and Kenny says," Well, what a Godda..." Kenny notices AJ and then says, "What a coincidence." Kenny begrudgingly decides to go to Wellington but doesn't think they should follow her and the choice is whether or not to go to Wellington, if you say no, Kenny basically kind of forces you to go anyway, if you say yes Kenny will agree but state they shouldn't follow the New Frontier member. either way you're going to Wellington because it's Telltale.
END
I don't know what Telltale is doing in their version of the flashbacks but I'm making an hypothesis for Kenny (for now) and Jane (later):
In my own pitch for the ending flashback: Kenny dies BUT he doesn't die like a punk, he dies protecting Clementine and possibly AJ from New Frontier members.
Shit goes down in Wellington after Clem and Kenny become members or something, and Kenny and Clem/AJ all escape Wellington but Kenny gets shot his shoulder and stumbles bit but keeps goings but he's bleeding hard and they all don't have enough medical equipment.
They all stop, New Frontier members are closing in and Kenny tells Clementine to go and protect AJ, you're kind of forced mechanically to leave him BUT here's my own pitch and it might be overkill so bear with me:
You play as Kenny in an action scene
Kenny fights and fights the closing in New Frontier members by himself in a brutal action scene and it's played very similarly to Lee's famous action scene in Episode 5.
Kenny takes a good many out but is exhausted and bleeding hard once it's over and lying on the ground on his knees breathing hard.
Then a large lined battalion of vehicle come in and a camera shot of a lined up group of gunners point their guns at Kenny.
Kenny snickers a bit while coughing blood and here are three dialogue options (Forgive me):
"Heh, fuckers."
"Live or die, I am the Walking Dead."
"I'll see ya, Kat."
Shot are fired and you hear a body plummet, you don't see Kenny die, you only see his hat in which the camera zooms in once it plummets to the ground, sad music. Clem and AJ run into the woods with Clem sobbing and crying.
END
I'm tired, I'll get to Jane in the comments, I'm not a great writer so correct me on some issues you guys have.