Liking that Wheeler approach
Another idea I had would be to go up Airplane Gully at night and leave a lookout at the top of Airplane Gully. Then under the cover of darkness head across the valley with the aim of hitting the Kiowa - Arikaree saddle at first light (I would think an average party could make it from the top of Airplane Gully to the Kiowa - Arikaree saddle in less than 2 hours). If you hit the Kiowa - Arikaree saddle at first light then you could do the ascent in the light and appreciate it. Meanwhile your lookout would be scanning for the fuzz. If nobody saw the fuzz then you could retrace your steps back to safety. If you encountered the authorities or saw them in pursuit then you could possibly head toward N Arapaho or some other destination and have your lookout pick you up at a different trailhead.
Of course this is all wild speculation, and I would never dream of partaking in any illegal activities.
I can't remember if i copied you my last e-mail to Chris about this issue but I'm not going to mess around with trying to outsmart the system. There's no way to get caught from Wheeler. They will never see you going up until it's way late. By then I'll be down in Wheeler again on my descent. No way they will chase you down into Wheeler, especially if they can't see you in the trees. Also, I'm so convinced that Wheeler's the way that I'm gonna do it whenever I want at whatever time of the day I want. I've been on the Wheeler trail and its a good one.