I actually think of San Diego proper as an old folks town and always thought those were the buyers that should have been targeted.
In fact for a few years that is exactly where my sister and BIL were planning on retiring until the condo prices went sky high.
Families I know who live in NYC and SF live in what I would describe as inter-urban neighborhoods – flats that are mostly occupied by families or they own a rowhouse. They are able to either get their kids into the top public school in the city or can afford $15,000 – $30,000 tuition. If I had the money that is exactly how I would live and raise my family.
But it’s nothing like downtown SD where I’d like to go visit Grandma but not live there.