A better use of sleeping in cities

[jayhova]

Is there a way to test to see if you can be found if sleeping inside a city? Let's say I sleep in the courtyard of someplace or on a roof or somewhere the guards are unlikely to find me is there a way to test to see if this is true? Maybe I could rest an hour or two and the guards might not happen by. I'd like resting to be a bit more complex that an immediate rush of a hundred guards to stop one guy from vagrancy.

I would also really like to see extra choices on sleep, like sleep until dawn and/or sleep until nightfall.

[Regnier]

that would be great, different skills and adv/disadv could be incorporated. Sleeping on top of houses would be cool.
Interactable objects in town could assist you, like you sleep in a tree for a couple hours and no one notices.

Ive also thought about people picking your pockets while you sleep, if youre not careful.

[Utankung]

I would love this sooo much!