Having been in an HOA home previously, I would never buy a house that has HOA if I can help it. While the board is essentially made up of your neighbors, that does not automatically mean they have your best interest at heart, or for the neighborhood for that matter. And to make any sort of impact on the decision making, you would have to campaign and get voted on the board and add that to your list of commitments. If not, you end up arguing with neighbors who ARE on the board and making your living not so peaceful. My HOA fees went from $90 to over $300 in a span of 5 years because the board voted to change mangement companies. The road outside my house got repaved twice in 4 years. My fence got torn down and replaced twice in 3 years. There were nothing wrong with either, in ANY of the houses that were affected. They were placed on the agenda for meeting obviously but to make my disapproval known, I would have to make time once a month and attend the meetings. I cashed out of our house in Sunnyvale last year and moved to Almaden, which is just south of Cambrian/Willow Glen. A lot more house for the money and the school district is only SLIGHTLY behind Cupertino/Sunnyvale. Traffic is much lighter around the neighborhood and much closer to the hills for hiking/biking etc. We also looked at Cambrian/Willow Glen but the areas that feed into the better schools are smaller and inventory was low. My wife works in LinkedIn so I understand your pain about the commute. But depending on the time, its not too bad. She can get to her office in Sunnyvale within 30mins if she times it right.