Akula,
Tough call. With respect to #1, call him to the mat during the training session. When he makes a snide comment, ask him how he would do it and remain safe and compliant. A second option is to dismiss is comment as irrelevant, "Bob's comment aside, we want you to be safe and here's how management expects it to be done."
With respect to #2, come in on the off shifts. From your post, it's apparent that you know the work is taking place. If you don't know when it is going to occur, ask the managers. They know when it's going to occur, they're paying the overtime. The first time you show up be gentle. Let the workers know you want them to be safe. Help if you can. The second time, if they're not behaving read them the riot act but don't write them up. The third time, write them up.
With respect to #3, not much you can do. The only thought that comes to mind is sit the guy down one on one. Tell him what you need and expect of him as a manager. Then let him give his thoughts and take them to heart. Some of them may be valid.
With respect to #4, you'll need four people in the room. You, the supervisor, his boss, and your boss. Let your boss know the supervisor is uncooperative and obstinant. Have a plan of action going into the meeting. Ask your boss to present the plan to the supervisor's boss. This takes away the supervisor's power because the meeting is actually between the two bosses. You and the supervisor are along for the ride. He can't leave or he'll lose face with his boss. He's at a disadvantage because you're boss is presenting the plan. Finally, if you can, make a minor concession. It will allow him to save face. SunTzu (The Art of War) always allowed his opponents an escape route. That way there was always the option not to fight and that often lessened his opponents resolve.
MikeCJ