Beware of youtube videos about connecting 2 compressors together

I think what you are calling a regulator is actually a pressure switch that turns off the motor when the pressure gets to the high pressure you want.

You should have 2 contactors one for each motor and use the one contactor to power the other contactor the pressure switch to turn one contactor on and off.

It's a combined compressor shutoff pressure switch and an air pressure regulator that has tank pressure available on one side and regulated pressure on the other. It's a really nice unit that they used to use on Sears and Montgomery Wards compressors with the C-H compressor back in the '60s through the '80s.

Maybe I didn't explain it well, but I'm already doing what you suggest. The pressure switch has its own set of fairly hefty contacts inside, which are 'way overkill for the minimal current draw of the second contactor coil.