Seems Scott just doesn't want to be dropped off.
Over the last few days I've tried to place him in four different caches.
Cache #1: Cache was to full and he wouldn't fit
Cache #2: Could not find cache
Cache #3: Cache was also full and to small for Scotty
Cache #4: Found cache plundered in middle of the trail. Just to find out later from the owner of the cache that was the original plundered cache and the cache had been replaced.
I'll keep trying to get Scott going.