Hi Red 5,
I am from that area (Willow Glen) and have 3 kids, ages 9,12 and 14. I am pretty familiar with the schools in San Jose, Campbell, Cambrian, Cupertino, Los Gatos and Saratoga. Feel free to PM me and we can talk more.
Picking a school is a big challenge. The public schools in Willow Glen are not high performers, so my kids ended up going private - Mulberry School in Los Gatos, Almaden Country School for middle school, and my oldest starts at St. Francis for high school in the fall. My brothers' kids have gone to 3 Catholic schools and are finally happy with Holy Spirit, in Almaden.
There are a lot of choices, depending on what you are looking for.