Season 2 should start at the same time Season 1 started. Playing as a different character, and a whole set of different characters in your group, and we could begin at Atlanta. Of course throughout the course of the season, a lot of crazy shit happens, and you ultimately find yourself in Savannah by episode 5, alone. Towards the end of the last episode you find Kenny being surrounded by zombies. It could be in different locations depending on your choices in Season 1. Then you could get a chance to save his ass, which would be a great opportunity for awesome gameplay (for those who think TWD lacks gameplay) Next, you escape Savannah together. The process of escaping Savannah is another great opportunity for kick ass gameplay. You finally escape Savannah and BAM! You and Kenny are the two figures Clem sees at the end of Season 1. And the season ends there.
Just a thought of what Season 2 could be like. Tell me what you guys think.