The hired steward at Windstad Manor seems to always sleep in the player's bed upstairs, instead of picking the left single bed on the opposite side of the upstairs area. For some reason, when it's time for bed the steward will get stuck trying to walk past the chest (0301200D) near the player bed and then go to sleep. I've watched steward behavior very closely in the other two manors (Heljarchen Hall and Lakeview Manor) and they're able to successfully walk past the mentioned chest and around to the other side and sleep in the left single bed. In case you're wondering, this problem occurs in Windstad Manor regardless of who you choose as steward.
What I'm wondering is if this could be some type of routing issue, specific to Windstad Manor.