I've tentatively chosen Mt. Bierstadt (14,060') as the initial 14er to map. Compared with the Matterhorn, it's nearby, has easy access and is relatively easy to climb. Mt. Bierstadt, however, has a more complex topology than the simple pyramid of the Matterhorn. I've put together a series of images that cover a 2 mile X 2 mile square centered on the summit. The first image above is a satellite photo from google maps.
The second image is a textured topographic map, also from google maps:
Looking at the topology of the mountain and assuming ground stations at the bottom of the mountain, it looks like it would require 7 different vantage points to cover the mountain while maintaining line-of-sight with the plane.
Assuming ground stations at the top of the mountain would seem to require 3 different vantage points to cover the mountain while maintaining line-of-sight with the plane.
This is all theoretical, of course, so I'd love to get some feedback on how to choose a flight plan for a complex mapping task like this.