I had a chat with a local architect, Bob Stoecker. Very interesting and inspirational. He said several things that immediately resonate with me:
First, a lot can be done to make the existing small'ish home seem bigger and more airy. One thing he suggested was to have all the windows go all the way up to the decking and all the way down to the floor + build a wrap around deck to give the illusion of the floor continuing.
Second, the true value of living here is the mild Mediterranean climate - begging for an unobstructed indoor-outdoor flow. So he recommend putting at least 100K into designing and building the exterior room. He pointed me to Ron Lutsko as a great architect/designer of modern landscapes.