In a previous playthrough I remember there was a presentation with Bob, and also I was able to work with Candy at Cafe 52.
I restarted a game recently and played until I reach the 2nd office party (I'm in August) and still, no presentation, no cafe 52, no coffee machine in Antler's office... Is there something I forgot to trigger these events, or is it random?
You must get the random event
event_work_first_coffee_work_1
(which introduces you to the coffee machine and your first shift at Cafe 52) to work at Cafe 52.
To get that event, you have to get the random event
event_work_admin_coffee_0
(which is where the coffee spill happens).
To get that event, you have to get the random event
event_work_meeting_stage_3_meeting_admin_1
(where Bob gives his presentation).
To get that event, you have to progress at least to the manager's 3rd stage (check in the console for
SugarCube.State.active.variables.npc_manager.stage
being 3 or higher) and have attended the previous meetings (check in the console for
SugarCube.State.active.variables.npc_manager.flags.meeting_stage
needs to be 3), and if you "Gather your things and prepare to attend her." and are wearing a remote plug when a meeting is about to start you'll trigger Bob's meeting.
Seeing as you have attended the 2nd office party, you probably just need to trigger the random work meeting events until the 3rd one where Bob presents. You can back-scum while working to attempt to trigger it.