Honestly #2 would likely be the best situation for the Wings in the long run, if not for Stuart, as you're right they'd likely get more in return. Unless he's part of a package deal for Ryan. But like you said, because people know he's a UFA who wants to play in Southern California, the Wings are not in a strong bargaining position.
If they go with #3 though, I hope they do make some big deadline move to take a serious run at the Cup before they lose Stuart and probably Lidstrom next season.
I think if his heart is set on going to his home state, then Holland MUST attempt to get something in return. I understand your guy's assesment of his pending UFA status kind of handcuffing Holland, BUT what if ALL THREE California teams want his services? It's not like he is chopped liver and he could be a huge help to any of them. So it's not like they are all gonna lowball Holland in and miss on a chance to attain his services. BUT if we are dealing away one of our top 4 defenders, with really nobody to replace him right now (Smith, Kindl or Commie are not top 4 defenders) we damn well be getting someone back that we can put in his place. This is why I cannot see Holland trading him at the deadline unless the deal is just too good to pass up. He be better off trading his rights in June. I'd personally chose Anaheim at the deadline if that is when he will be traded, 1. We won't have to worry about facing them in the playoffs and 2. Since they are looking to sell, they could outbid the other two playoff bound teams who would rather be buyers than sellers and upsetting the chemistry on their team.
With that being said, I really wish Brad would stay, but do understand (personally) spending time away from your family for your career. What ever happens, Brad will be remember as one the best defensemen we have had in Detroit and he will always be a Stanley Cup Champion as a Detroit Red Wing. Godspeed Brad Stuart!