Since you have to have an automatic, that'd steer me to the Prius by default.
I'd say start searching now for a gen 2 Prius, and be prepared to buy when a good one crops up (one will). You'll enjoy it much more than a Fit (I don't want to read your constant complaining about their undergeared transmission needlessly sucking away precious fuel!
). Plus the Toyota has an excellent reliability track record.