I've said somewhere else what my ideal Season 3 would be, but I'll do it again.
Way things are looking, I don't think we're going to make it to Wellington by the end of this Season. I mean, we might, but I'd be mildly surprised, going off of the achievements.
So either this Season ends with us reaching that town, at a relatively safe place, with whatever characters are still alive planning on going to Wellington once the snow lets up. Or, we make it to Wellington, and we end with the remaining characters entering Wellington.
Season Three I suspect will either start at the town or Wellington, after the winter(no big time skip), and if we aren't at Wellington already, then Season Three starts with them just getting ready to go there, maybe some new character, either someone we know(Eddie, Nate), or someone new(similar to Mark in S1E2). First episode will focus on getting there. Or, if we're there, then... Well, that would basically be the same of what I expect episode two of this scenario would be.
Once at Wellington, I suspect at the least we'll have been left with at least Clem, the baby, and either Luke or Kenny.
Ideally, I'd like it to be Clem, Lee Jr, Kenny, and Bonnie, but most likely not.
Once we find Wellington, it turns out that it's similar to Woodbury from the prequel novels. The "wild west", a safe place, but with no organization or leadership. Both Luke and Kenny can be seen as leaders, so one of them taking control I think would be the general plot once were at Wellington.
Kenny Alive: He tries to take charge, a few people(or one person in particular) don't want Kenny in charge. E1 or E2 story arc, 1-2 episodes. Luke Alive: Same as with Kenny. (Not saying that there should be a Luke/Kenny choice, and then have them be determinant characters with mirrored plot lines) Both Alive: A power struggle is created between Luke and Kenny, Clem or new protagonist chooses who to support. E1 E2 story arc, 1-2 episodes, but also something lasting throughout the Season(If Kenny takes charge, Luke is bitter about it, vice versa) Both Dead: Some corrupt leader is in charge(again, similar to Woodbury prequel novels). E1 or E2 story arc is taking him down. 1-3 episodes.
Possible protagonists would be Clem, Bonnie, Mike, and then to a lesser degree, possibly Kenny or Luke(not something I'd like if both were alive, but would be interesting to be put in the position of the leader of a large community). OR:
Disregarding the previous suggested starts, the main character is someone new, who has been living in Wellington for a few months. We get to see Clem's group from a new angle, and they are all major characters, maybe with Clem as the deuagonist for Season Three.
Other possible plotlines later down the line:
A proper war with another large community(Around E3 or 4 we meet another community or large group of bandits, this culminates into a big fight during the Season finale, and maybe Wellington falls, and the survivors flee, similar to the prison in the TV show/comics) Herd(kind of boring, but eh) A group of strangers show up around E3 or 4 and start tearing the community apart(similar to what I expect Magna and Luke will do in the comics.)