Eleven months of interviews lost because of resume formatting? Sounds like maybe those jobs just weren't calling back.

The start relay and run cap thing is close but not the whole story there. Low amps on a compressor usually points to it not pulling its load, which sounds like a weak winding or a dead run cap more than the relay itself. The relay is what sends power to the start winding, and if it fails the compressor just hums and trips overload, it doesn't quietly run light. I ran into this on a Sub-Zero last year, amps were sitting at 2.1 when the tag said 8.4, turned out the run cap had drifted way off and the compressor was barely turning over. Replaced the cap and amps came right back up. The relay was fine the whole time.

12 gauge on a 250 amp winch is crazy, that's like trying to drink a milkshake through a coffee straw. But I gotta say the wire size probably wasn't your only gremlin, a winch that size needs a solid ground and good connections too, and a lot of guys upgrade the cable and still cook em because the terminals are loose or corroded. What voltage were you actually seeing at the winch under load, if your buddy had the clamp meter did he get that number? Cause if it was dropping to like 9 or 10 volts that tells you more than just the gauge.