Nice trip reports: We did a similar trip mid September or first to Chile and really loved the place.
Like you we stayed at the San Cristobal and must agree the staff there really know how to attend to ones needs ( without giving the
impression of fawning over you)
One place which they highly recommended and we were very pleased we followed them was an afternoon visit to Los Dominicos, the artisian village east of Los Condes we ending buying a lot of nice little Xmas ( unique for the USA) gifts at very reasonable prices. The guy who carves sport figures, automobiles or animals on match-sticks is unbeliveable.
I agree with Valpo but we were lucky to make our visit on a Sunday something I would highly recommend for day trippers, parking was easy, we parked at the foot of Asencor
Concepcion and had a great lunch at Cafe Turri right at the top of the aformentioned asencor with a fantastic view of the harbour.
While i agree with you summation re hotels outside of Santaigo we did stay in a great place called Hotel Plaza Santa Cruz (in Santa Cruz of course) right in the heart of the wine district. The place is sort of the unofficial hangout from European and Ausralian wine merchants.
Finally one other side trip which in involved driving about 60km up into the Andes from Molina was to go to Siete Tazas.
This is park is set around some spectacular waterfalls and in one location has water cascading into seven stepped pools hence siete tazas = seven (tea) cups.
Well enough from me I dont want to hijack you trip report.
mike