Once in a blue moon problems are the worst.
Get an inexpensive volt meter (or three), attach to yea olde gear motor and leave it sitting between the seats. Next time it happens, you can look at the motor (and pressure switches, and solenoids, and...) and see if it is getting power. If it doesn't move the meter upstream, etc. Eventually you should be able to narrow it down.
I would have suggesed that you tie a bosun's chair to the struts so your mechanic could observe from outside, but your airplane has a strut deficiency.