I know the 2 homes you're referring to that's on the market. I think it depends on personal preference. The lennar home is in a nicer condition and has more decorative upgrades. The Emory home has more bedrooms and bathrooms and is larger in size. It all depends on how many people you have in your family, how big of a yard you need and your preference with the floor plan. If you don't need the yard, then it's just more maintenance. There are plenty of parks nearby for that the kids can plan in.
Personally, I like the Lennar home better because of the lot size and it's in move in condition. From a builder's perspective, Brookfield tends to have better quality.
Overall, I would wait until next year. The inventory is growing in Windemere and the prices are coming down. We're likely to see more of that in the next couple months as more short sales and bank owned homes hit the market.
"Also, the one with smaller backyard has a bedroom downstairs and the one with larger backyard doesn't and the rooms are much smaller. "
If you have an elder family member that will be living with you a downstairs bedroom would be ideal so they do not have to traverse stairs. As far as the "bedroom size versus backyard size", this is again a personal choice based on what you have seen, an individual's needs as far as bedroom size is also personal.
"Another tough part is that I will have to rent it as I cannot move immediately since I currently rent in Cupertino and my children go to the best schools here and I will take 6-8 months to move to San Ramon."
With the current condition of the local economy, and the resulting state of the housing market, I would NOT buy now if you have a 6-8 month timeline for moving (a lot can happen in 6-8 mos time). Instead, I would suggest saving the cash you would have expended, avoiding the stress and hassle of finding/managing tenants, and using the next 6-8 months objectively studying where you definitively want to live.
Also, the one with smaller backyard has a bedroom downstairs and the one with larger backryard doesn't and the rooms are much smaller.
Another tough part is that I will have to rent it as I cannot move immediately since I currently rent in Cupertino and my children go to the best schools here and I will take 6-8 months to move to San Ramon. Is it a right thing to buy a home now and take the headache of renting it out to cover the mortgage or wait until children school gets over next year i.e. don't rush now even if maybe good deal ?