If I ever had questions about whether my Google Earth-derived backdrops were appropriate, I've now got the source material. The Santa Clara County Pioneers have uploaded a promotional video for Redwood Estates from 1927, and there are some nice panoramas of the hills as well as detail shots of Los Gatos Creek and the area around the Redwood Estates vacation subdivision. The hills look a bit more brush-covered, but it looks like the current backdrop won't need to change.
And if the prospect of clean living and a windmill wasn't enough to get you to buy a lot in Los Gatos Canyon, they also have video of Los Gatos proper. Video of the Los Gatos train station starts at 8:00.
The Blossomtime in Santa Clara County is also worth watching. It dates from the 1950's, but highlights how I ought to be thinking about what's under the trees. I've been leaving it as bare dirt but the videos show orchards with high grass (winter), short grass, and plowed earth. The San Jose Chamber of Commerce must've really liked those time-lapse blossom-opening videos, because they're sprinkled liberally through the film.