I finished Season One this week as it was the Gold Deal of the Week, and I really want to play Season Two. Should I wait and play the DLC or should I jump straight into Season 2?

Keep in mind, I only have enough money for one (Yes, I know).

Yes, personally enjoyed it more than the first episode of season 2, and maybe a couple season 1 episodes too. It does short stories really well. Also...how does spending five dollars make spending 25 impossible? Maybe hope it gets discounted a bit in the Steam sale?

I would recommend you get 400 days now, then wait until Season 2 is completely released before buying it. What if the last few episodes of Season 2 are really bad? Not much reason to get invested in the story by playing the first few episodes, in that case. 400 days is entertaining on its own.

You could buy it if an hour and fifteen minutes is worth your five dollars or wait, episode one will be free in march when they put out episode two, maybe 400 days will be too. or you could play the wolf story its much better. Then again better stuff is five dollars on 360 right now.