On re-read my manual says to put silicone grease in the gear box via the screw in grease cap on the mounting base up in the roof. The solvent used to suspend the silicone lube in many of the sprays out there can be very damaging to the plastics used in the elevator assembly and may have embrittled it causing your problem however the plastic parts only seem to align and don't really seal against weather.
I do see that the current manual says to use spray though:
http://www.winegard.com/kbase/upload/2452013.pdf
Time to open it up and see whats going on there. You may just need to replace the 2 o-rings, reseal the base plate to the roof or you may have some damage from a low tree branch or high wind situation that has to be dealt with.
Check out groups 7 & 8 in the parts diagrams on page 7 of the linked manual to scope out where the o-rings are located and how the elevator goes together.