I told my sister and her husband that buying a canyon view small home in Clairemont with some character would be better than buying a faceless home in 4S Ranch. A bigger lot would allow some quality outdoor time (especially with the gorgeous weather that San Diego has). And you could do a remodel with some of your own architectural ideas.
Unfortunately, (in a typical Asian fashion), my brother in law wanted to buy a “new house” to impress his side of the family.
To each his own.
But I think my analysis would parallel yours quite a bit.