Sorry Matt my reading of your last paragraph was kind of hair raising, picturing a plug end on a length of romex and coiling it back up when done. To minimize VD to protect your tools go with the 6/3.
As for your last question, check your local code for what's doable. and PVC conduit will save $$ vs metal if its allowed. Keep in mind that the longer the run the greater the VD.
What does it mean when you've accumulated enough tools that human life expectancy precludes you from ever getting truly good with all of them?