My Season 1 to Season 2 import fix (Mac)
This may be obvious to some, but it took me quite a while to solve my problem, so I figured I’d share it here...
I couldn’t figure out why my TTG purchased S1 data wasn’t being imported to S2. I reopened the original S1 .dmg file in order to reinstall the game and noticed that the game’s file name is, “TheWalkingDead” (No spaces) and remembered that I had changed that to, “The Walking Dead” (With spaces). This caused the saved games folder (~/Library/Application Support/Telltale Games/TheWalkingDead/) to be incorrectly titled “The Walking Dead” (With spaces) and the S2 game couldn’t find the correct data. Removing the spaces from the file name of both the application and the saved games folder solved the problem.
Hopefully this post will save others the headache I went through trying to figure out my problem. (If they change the game's file name like I did.)