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The one on there that keeps failing is more than likely all crudded up and nasty inside. I experienced the same thing on my tractor but, guess what; it was in the heat of summer. Point being, they fail when they get old and corroded up not just in colder weather. They're cheap so just get a new...
It has to come off. Separate the valve, ( it's screwed together ) push out the ball, ( it is slotted on the top where the stem is ) then push the stem down and thru the valve body to replace the o ring.
Try removing your expello valve on the dryer and cleaning the gunk out of it. Or better yet, replace the dryer with a new one. You'll have a lot less headaches in the end.
Sounds like your tractor protection valve diaphragm is bad. An easy repair.
http://www.steelsoldiers.com/showthread.php?144109-Air-Brake-Protection-Valve-leaking-venting
You're going to have to get the pulley off to see if the shaft and/or keyway is damaged. Maybe just the pulley is but if the shaft is, might as well start looking for a replacement alternator whether stock or aftermarket. It's not a big problem replacing it either way though. Feel free to call...