Anyone ever consider giving X-Marks or a similar "underground restaurant" a chance? I've visited X-Marks a number of times before going Paleo and they do wonderful things with food. They cater to any dietary requests, and if a large enough group attend on a night, they'll customize an entire 5 course menu to meet any request.
I think it's about 20-25 people to rent out the place for a night to do a fully customized Paleo menu (i.e., not just remove gluten from the current item, but they'll design the menu from scratch to meet the requirements based on what is in season and available that day in the market). If you just show up on any other night, they'll take their existing menu and adapt it meet dietary requests. It's around $70 per person, BYOB, great service, great atmosphere, and great food.
They also can meet individual requirements if you do rent it out.. If we did a Paleo night, some people can choose dairy free, some (or all) could do gluten free, vegetarian, vegan, etc.. they'll happily meet any or all requests on a per person basis.