There are so many people moving from the Santa Clara County to San Ramon. You can get a lot more for your money in San Ramon - a bigger and newer house, bigger lot and excellent schools. Of course, you have to be comfortable with the commute. You can certainly take BART from Dublin/Pleasanton station to San Francisco so you don't have to deal with the freeway traffic.
At this time I have 4 clients looking in San Ramon. There are some really good deals in Windermere and Gale Ranch. Prices have come down a lot and buyers can see the great deals they can get now. Most properties are selling with multiple offers. We just wrote an offer at asking price on a property listed for $907K in Windermere San Ramon and it sold with 22 offers most of them above asking price.
As far as waiting till end of school year, if you are looking at a short sale property, it can take 2-4 months (maybe more) for a short sale approval. So by the time you end up closing the deal, it may be the end of the school year anyways. So you may want to start the search now.
As far as kids and their music lessoins etc., Windermere is a very family orientated comuunity with so much going on. As a matter of fact there are many dance schools in Dublin( teaching Bhangra, Bolywood, Kathak and Bharat Natyam). There are in home music and singing lessons available.
I used to live in the San Mateo County for 18 years and moved to the East Bay in 2000. I used to wonder how I would get used to the changes, but believe me, it is the best thing I ever did. My daughter had more exposure to dance classes ( Bhangra, Bollywood, jazz, Hip Hop), singing lessons, soccer, Tennis, basket ball, swimming and horse back riding in the East Bay than in the San Mateo County.
If I can be of any help in showing you homes in Windermere or Gale Ranch or anywher in the East Bay, you can reach me at 925-425-9491