Why does this require a different level of support than just having crew member A and crew member B on the ship together?
I think Gedan just means in terms of practicality. I'm sure if it's a very specific sleep/wake-up scene that plays with very specific set of parameters, then that can be implemented with no issues at all. It's just the prioritization of these events that's the issue--especially if Steele has more than one crew member who all have possible sleeping/waking events. Because what happens when you have followers A, B, C, and D, where A+B has special scenes, C+B has special scenes, A+D has special scenes, A+B+D has special scenes, along with all their individual scenes... Which one takes higher priority? What if one in particular is tied to a mission? What if all of them play simultaneously? If more than one get triggered at the same time, it would not make sense chronologically.
A potential simple solution might be to work the sleep/wake scene selection into a kind of roulette, so that out of all the available and possible scenes, only one scene is picked and plays out (assuming a higher priority scene is not triggered first since not all scenes are triggered the same way). Like Gedan mentioned, something like this wouldn't be hard to implement, it's just that there isn't any content to justify such a method (there are only single scenes so far...). So until there is a need for it, then it is currently not practical to implement.
So from what I gather, you can write such scenes and provide a clear enough picture of all the conditions involved to trigger them, but the scenes' implementation will be questionable unless it is required (like for a quest or something similar) or until there is enough of those kinds of scenes to garner a new system to help handle it.