1. 0.5.5.3a (version #58310 (osx-public))
2. macOS 10.13.2
3. Around day 11, with 7 residents, "Leave to Town" stopped working. Clicking the button or pressing C does nothing.
4. Not sure how to replicate it, it just stopped working.
5. Saved, closed the game, loaded the save, same thing. Now on day 76, still can't leave to town.