Well as you know I am one of those guys who knows what he doesn’t know and I simply do not know about the Wisconsin market so for me to speculate on what the future will hold for that part of the country would not be prudent.
All I can do is speculate about La Jolla and San Diego in general. Having a family with children I can sympathize with your situation all to well. I absolutely want to be in a home and not of the renting variety by the time my kids hit school age. The one thing I would say is that once you do move you should be prepared to stay there until the kids graduate but it seems like you are planning on doing that regardless.
So let’s throw out the usual reasons to stay here such as weather and such because these factors don’t seem to be tugging at you anyways. I guess the real question is, which market will depreciate more, Madison or San Diego? Tough call because I simply do not know Madison. I will say this, I do not believe La Jolla will be at the bottom next year, or perhaps even 09. I do believe more of the risk will be removed by 09 but to me, I just don’t see bottom by that time.
Anyways I don’t think your crazy at all and I absolutely understand the reason for your purchase. To some people life is not only about money. You are not a first time buyer and it seems like you can afford this. Everyone has a unique situation and for your situation this seems like a perfectly logical thing to do. Will Madison go down more? Probably but I have no expertise at all in that market. Perhaps you should research it out or work with an expert over there.