All great places to surf. IMO Jaco is easier place to learn to surf. All three are very different from eachother.
A very easy way to do this would be to fly with Nature air from San Jose to Tambor (Santa Teresa) stay in this area for a few days then fly from Tambor to Nosara then fly back to San Jose. This is a quick and easy way to get around, pluse affordable if you watch for good ticket prices. I haven't been to St. T in September but from what I have heard from friends the rain can sock you in. This option probably keeps you in San Jose the first and last night of your trip.
Another option would be to go to Jaco once you arrive. you could stay a few days then take the taxi boat over to Montezuma on to St. T. To get back to San Jose you could fly or ferry or taxi boat back. This option would only have you in San Jose for one night.
IMO it depends if you want to be in a quiet/ more secluded area the whole time or would you like 1/2 and 1/2. Jaco is the biggest beach town. Lots to offer, especially for surfers, but you won't feel like you are in the middle of no where. I leave in less then a week and will be flying into Nosara then drive back to Jaco.