Sounds like you have a electrical gremlin, as you probably already suspected (comment about grabbing the multi-meter).
Has it ever failed when trying to put the shield down? If not, then you may be able to narrow the search to the relays (either could be at fault), the handle bar switch, and the wires between them. Gently tugging on the wires while trying the switch could induce the failure, if it's a bad wire or connection.
Otherwise, you might want to poke around the fuse boxes under the seat, and gently tug on the wires around the windshield fuse (box 3, fuse 4). Also take a close look at the fuse itself.
Next time it's in the fail mode, tap gently but firmly on the relays while pushing the button to test. If it suddenly starts working, you might just have a bad relay.
If it only fails in one direction, you can pretty much rule out the motor, as it's only two wires, and the relays change the polarity to the motor.