Yep, need larger wire before uping the breaker size.
You mention a Craftsman auto switch? Is that the one that has two tools pluged into it and when one is turned on, the other tool is automatically started? If so, I have one too!! LOL I "thought" I had a problem with the motor on my 6X48 sander so I replaced the motor 2 days ago. Guess what.....still tripped the breaker (20amp!) every time I turned on the sander. Shop vac was plugged in the Craftsman switch. Come to find out, if I yanked the auto switch and went directly into the outlet, it works fine. You might try that. Mine apparently is slowly dying. Had it for maybe 6 or 7 years. Liked it but seems it's biting the dust. Staggering your startup load may do the trick.
Congratulations to Mr. "the sky is falling" Al Gore, nominated the new Village Idiot!