STM,
This can be a very good combination for how most people cruise their boats (i.e., coastal). Most racers would want more flexibility, but this arrangement is not usually offered on flat-out race boats. The mainsails on these boats tend to be larger to provide much of the drive upwind, with the smaller
jib helping out. And then you get to "switch gears" for the downhill leg and quickly spread more canvas.
Saga and Tartan offer this headsail combination, and I've heard generally positive feedback. Personally, I wouldn't mind this set-up at all, although I wouldn't necessarily insist on the self-tacking aspect. Also, it generally works better when the downwind sail is tacked at the end of a longish fixed sprit, but most designers and builders seem reluctant to use long fixed sprits nowadays. About the most you'll see is an extended
anchor platform.
I think Tartan calls theirs the CCR for "Cruise Control
Rig" (which sounds a bit silly to me), and I really like their new 4300 on which it's offered. I think it's also available on their 3400, maybe some other models as well.
Edit: Ah, I see you posted the boat model while I was typing. I think that would be an almost ideal sail combination/boat for cruising the Chesapeake. Lucky you.