If you use a magic Start Detector or a Player Detector
(The former is probably better here), you can set it up so that the Player is teleported to the jail cell!
As for decoration tips, make sure to cover up the windows! With the cramped space, heightening the immersion is crucial to a successful dorm. Covering up the walls, making a small path through the middle with features on either side, and using Advanced Movement in conjunction with Castle Magic is key.
I would recommend looking into the Black Rock Shard housing item personally. Oh, and be sure to utilize Monstrology Guests! There are tons of multicolored ghosts out there.

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