Buddy Issue

As far as the buddy issue, you are on the right track with this:
 (I feed the horses separately and alternate putting them out together and in different pastures; or one stalled and the other out.)

When riding you can practice having the other horse trot off ahead and you stay behind for just a few minutes then come back together at a walk before either horse gets upset.  Then switch positions and you trot off ahead.  As they build confidence being separated then gradually make the separation time longer and farther away.  There are lots of variations of this exercise - turn around and go back down the trail or spread apart in a big field while still heading the same direction, etc.

When riding him by yourself you could practice riding away from the barn and resting out there then riding back to the barn and working there - side-pass, backing circles, etc. so the barn is not a great place to be but riding away becomes the resting place.  Repeat this several times in a single ride so you keep him guessing about when he is actually going to get to stay at the barn.

Enjoy the Journey,

Ed Dabney is an internationally acclaimed clinician, presenting horsemanship and riding clinics all over the US and in Europe.  In 2007, Ed was named Champion of the East Coast Trainer Challenge Series by Equine Extravaganza.  Ed was honored to have been selected by the University of Georgia to teach their senior level Young Horse Training course.

His training articles have appeared in many major national magazines.  Ed produces instructional videos and the “Gentle Horsemanship” TV program which has been seen on RFD-TV.

Ed's blending of natural horsemanship and classical equitation has made an indelible mark with students all across the United States and now also in Europe, drawing the attention of serious riders searching for the lightest touch and the deepest connection with their horses irrespective of breed or discipline.