GPS will always assume a flat (although not necessary level) distance from one point to another. Therefore if there is a hill between points, the GPS will "flatten" the distance, and the actual distance over the ground will be greater than the GPS distance.
GPS accuracy is quite dependent on the signal quality. Newer GPS systems use WAAS (Wide Area Augmentation System)technology which is accurate to 2 - 3 meters horizontally. This accuracy factor is is not clumulative - so over 5k one might have a 2 - 3 meter error, and over 26 miles the error would also be 2 - 3 meters, but the distance would be from one point in space to another, without regard for distance traveled over ground. (Remember that GPS was developed primarily for aeronautical purposes.)
A good GPS would certainly be a useful tool for laying out a course, to be finally measured by established practice.
Dick Blum
ryblum@mchsi.com