I just had something rather interesting happen. I had basically been using Valdimar as my "gopher" for all three of my manors, and got them all built. But after I was done, I decided to go ahead and try to get a steward for each of the other two, and when I fast-traveled to Heljarchen, Gregor just happened to be walking up to my manor. I talked to him, and asked him to be my steward.
Pretty cool - something I was not expecting. Maybe he was on "patrol" or something, or maybe the game decided I really needed a steward and sent someone it knew could be one.
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