I'm currently on a Cannondale Synapse.
If I were in the market right now, I'd be looking at a gravel/adventure road bike. I wouldn't consider anything with traditional caliper brakes, and I'd target a higher end hydraulic setup rather than a mechanical setup. Take a look at the Specialized Diverge?
The major issue I've been having with mechanical disc brakes is that they don't self-adjust. For long descents (~2000ft), pad wear has been significant and noticeable. I've had to rectify it with slower wearing stintered pads. Hydraulics by comparison provide significantly better and more consistent feel.
I suggest more of an adventure bike for the tire clearance and geometry. My synapse will accept up to a 30mm tire, but options for CX tires open up significantly once you hit 35mm or so. The bay area has a lot of dirt trails that are great for road-biking. If you have the gearing, tread provides a significant advantage for climbing, and a lot of confidence on the descents.
I'd also suggest a compact crank with an 11 speed group-set, targeting a 34/50 front, and an 11-36 rear. 11 speeds is not by any means needed for classic 12-28 gearing, but with wider range gearing the extra speed makes it much easier to find the right cadence.
FWIW, I'm overweight right now, and my gearing reflects that. If you're fit, a 11-30 or 11-32 is probably fine.
I would advise avoiding Cannondale. My bike has been hard to maintain, parts availability isn't great (E.g. few companies make seatposts that fit,) and they have been very slow to deliver common components such as derailur hangers.
Also, I have to pull the crankset to replace my cables. That sucks.
Eric- Those look nice! I'd like to ride a steel frame, as I've always owned aluminum or carbon.
If you're looking at carbon price points, have you considered Titanium? It has a lot of the same characteristics of a steel frame, but at a much lower weight.
