sf2sd, I also moved from SF area to SD and been here for 4 years. I used to lived in Russian Hill, Fremont, and Santa Clara. SD reminds me of the peninsula, must slower and less hassle than the city.
One area you might want to consider is Carmel Valley. This area has newer homes than Del Mar or other coast areas. You will definitely find a very nice home for less than $2M or more than if you look for custom build. School here is also excellent and within the same Del Mar school district. As for hotel, try the Grand Del Mar. You will find many custom homes as you drive through toward the entrance of the hotel.
