So when I bought windstead manor, I also chose to have Valdimar as my steward for the house. Later, I bought Heljarchen Hall, and was given the option to move Valdimar from Windsted manor to be steward of heljarcken hall. He moved there, all was great.

I decided I wanted Valdimar back at windsterd manor, but was not given the option to move/transfer him back to windersted manor. Fine, I asked him to follow me, he did, and we proceeded to fast travel back to windstread manor. (Maybe he needed to be on the property to take the transfer). After getting back to winestred manor, no transfer option appeared, so I said "it's time for us to part ways". Valdimar accepted, but he responded to me by saying...

"I'll head back to windstad manor"! We were already presently at winsteas manor, so I thought he would just stay. Instead, he just upped and walked his old a$$ back to hallmark hall! I think this is a bug. He said he'd head back to Windstad Manor but walked to Hjallmarch Hall.

I'm married to Lydia, who was living at Windstad manor, and I thought it would be cool to have two warrior followers at my house(Lydia,Valdimar) at the same time for some good protection. Really, I just want to do some recon on my own house because I suspect she's cheating on me when I'm out taking arrows to the knee to support her stupid little store that she supposedly has that I can never visit.

ugh. cool story bro.

I have never seen any option to move a steward to another house, only a spouse. So yes it is probably a bug that you could move him in the first place now your Windstad Manor has no housecarl and possibly no Steward. I would just wait and give him a chance to end up at the right house, which would be Windstad manor.

I wish there was a mechanic to invite people to live at your longhouse. It would add a lot more value to the additional bedroom wing.