Please email email@example.com, with a description of the problem and the report.zip file generated by the D:OS support tool
(for the PC version). The report will contain system and game information, any crash dumps, and your saved games. File size may be an issue, especially if you have all your saves from the first playthrough, but you can selectively delete saves from the zip. I think it would help to at least include your first and latest saves from this game and your latest from the last (if available), and more would probably be better.
I don't think Clobbering Time is a guaranteed drop, but you should have gotten it in that many reloads.
A couple people have reported the map shroud or quests carrying over to a subsequent game, but it is not reproducible.