A few ideas --

Well, really, racers with drops and a deep saddle-to-bar distance wouldn't be using it if it weren't comfortable enough for six hours of training a day.

It's also nigh-impossible to put drops on something like a Townie and expect them to be useful. A big part of fitting them is getting a seat tube angle that's steep enough so that the angle between the legs & torso doesn't get too tight. If a particular frame has a more slack seat tube, getting a deep saddle-to-bar drop that's comfortable will simply be more difficult.

I'm honestly not too enamored with shallow drops, either. I think they're just compensating for a saddle-to-bar drop that's already really deep, usually deeper than what was on bikes in the past. I don't expect that the bottom of the "hooks" is really any deeper than the same position in traditional drops on an older frame.

There's also the rider's posture to consider (I don't mean position, I mean their posture in a given position). There's a reason why good fitters will say to relax the arms and put a slight bend in the elbows -- not only does it give some suspension to the front end, but it also reduces the rider's tendency to droop their upper spine below their shoulders. gecho, I'd guess that that's really what you're doing to make your neck hurt. If you take the load off your shoulders (rigid arms only end up transmitting loads to the shoulder joints), you should be able to get a more natural alignment in your upper body and get that crick out of your neck.