I finally figured out why it never appears that my saddle is fitting correctly....
Endurance saddles are usually equipped with center fire or 5/8 position. The 7/8 rigging that is on most trail saddles won't work for endurance riding -- endurance horses need the full range of their elbows, without a cinch too near them. Western saddle rigging tends to pull straight down, putting more pressure in the front of the saddle, but the rigging on endurance saddles should pull more from the center of the seat. Quality endurance saddles will have a rigging system that avoids bulk under the rider's leg, eliminating chaffing and irritation. Remember that center fire rigging requires a rather wide cinch (6-8 inches) to keep everything in place.
It has a rigging double rigging that I haven't been using (to do a v rigging). I've been cinching up the traditional way and not using the other rings. Also, from the description about endurance saddles (above), it does sit farther back from their elbows.
Does anyone know how many times to loop in in the front ring before using the back ring?