I'm having the same issue; a black screen whenever I try to start the second chapter on my second play through. I found the two pref.prop files (one in steamapps, the other in the Telltale folder with the saved games), I might have effed up though. I replaced the one in the install folder with the one from the saved games folder, instead of vice-versa and... did not back up a copy of the old pref.prop that had been there. :<
The pref.props should be synced now, but it erased my progress on my second play through, which, as it turns out is no big deal since I can still rewind the one from my first game. But whenever I did rewind and try to start the 2nd chapter, I get the same black screen issue. I tried looking for extra pref.prop files in the install folder (which if I'm right is the one in the Steamapps folder) but was unable to locate any. Any advice?
Also thanks for volunteering to help all of us lost souls!