A clarification in game would be very helpful. maybe a tutorial on your first level up, or on the menu when deciding to accept or decline there is a message letting you know if this obligation is rerollable or not.
An in game list of obligations, their requirements, and their rarity, would be super nice. Although it should definitely only unlock after you have seen that obligation at least once.
A weekly post on what you want to add to the game in terms of events and scenes would be awesome. Maybe have a poll here or there for community ideas.
and as far as officer personalities I think its fairly obvious, nice officers don't want anything (yet), sleazy officers want to fuck, and stern officers want to humiliate/degrade. It would be cool to hear how you want those "relationships" to progress and if they'll have split paths or anything like that.