Sometimes it takes an investment of time and, unfortunately dollars, to solve some of these problems. I have a mare who had behavior issues. A couple of trips to an equine vet, who is also an equine chiro, uncovered and corrected the problem. She was much better after treatment and rest.
Seldom do any of us get to sail through a life of horse ownership without encountering periods of concern and frustration. I feel for you. It isn't fun...but it is what it is.
I hope Sailor recovers with rest and you can get on with your plans. But I would certainly be surprised if he was giving you grief on purpose. Take this time to just love him up and see how it goes. : )