On my second playthrough and this is the first time coming across this bug. I did some testing for those interested and it seems to be related to dealing with the guards and choosing the non-hostile quest ending. Some key points below when I tried to replicate the bug;
- First playthrough was a skulker, silently took out guards, obtained VIP token, explored. I skipped the whole doll encounter, checked around Ev's room with Johnny, and came across Woodman on accident. I chatted him up, beat him with my fists to knock him out, then fought my way out of Clouds violently, no bug.
- Second playthrough, same as the first, skulker, skipped doll encounter, silently took out guards until not a single one was left. Picked up the cocktail stick, all of Ev's things, shards etc.
- Got to Woodman's office, turned around and went to do the doll encounter just to see what it was like. Followed up with Tom.
- Confronted Woodman with Corpo option to cut a deal. We finish the convo, game bugs, no objective in the journal and I can't retrieve my weapons or leave the front door, stuck in Clouds.
- I reloaded to before doll encounter (after taking out guards), skipped doll, same bug. I tried doing doll, skipping Tom, same bug. (Corpo deal option).
- Reloaded a fresh save right after depositing my weapons into the locker. Essentially started over.
- Progressed the quest objectives as the game suggests you should but without touching a single guard. Doll encounter > Ev's Room > VIP Lounge with Tom > Woodman's Office > Corpo Deal. Objective finally updates with 'Leave Clouds' as it wasn't before, all is normal and THEN I skulk around and loot the Katana, Ev's stuff, shards, etc.