Always. Typically I'll play through the game once in the lead up to release of the update, then the new content, then go for a full run again (Caribdis updates previous content a lot so there's some fun lines you can miss by never going for a full updated playthrough).
Nah bro u gotta play 0.8 now. The ending is just that epic.! It won't have the same effect when U continue directly to 0.9 after that scene. So u should definitely play it before 0.9
