My for-real experience with gear issues occurred a few years ago. In retrospect, the gear of my V-tail Bonanza never fully retracted. A flat spot in the motor-transmission interface hung it up in mid-retraction. It was a short flight, and when I flipped the switch to drop the wheels, it was clear that nothing was happening. My older Bonanza has a single red light to indicate gear-up (as in 'unsafe') and a single green light to indicate we're ready to return to mother Earth with the full benefit of the rubber bumpers. The motor wasn't humming and the red light stayed on. I overflew my Unicom-only (see, I didn't say 'uncontrolled') airport and asked for the folks to step outside for a look. Steve Parker confirmed that the gear appeared partially extended.