Second ride went much better today.  I found out from the first ride that we need more prep work on the right side.  Left side is great, right side has the sticky holes.  We did some exercises moving the right shoulder in and bending it around out of the way, (instead of his normal wielding it as a snowplow and trying to bull into me with it).  It worked successfully and we had an uneventful ride both ways today.  Making progress...