I think we're making this way more complicated than it needs to be for the OP's issue. :laughing: Michael just wants to paint his shed with a Graco Ultra 395 PC airless sprayer. I'm no sparky, but I can use an online voltage-drop calculator well enough.

If he plugs a 100-foot 12AWG extension cord into a residential duplex receptacle producing 120v at his house/garage, the voltage drop will be slightly less than 5%. So usable voltage will still be slightly more than 115v. The specifications of the Graco Ultra 395 PC call for a voltage of 115v. That assumes that the useable line voltage delivered by the Utility in Michael's area, Colorado Springs, is the typical 120v/240v (nominal) for residential service.
If he uses a 10AWG extension cord, voltage drop will be only 3v, resulting in 117v at the sprayer. In addition, that Graco sprayer is a commercial unit, intended for all-day-long professional use on construction sites. Michael can call Graco and speak with a tech rep if there's any question about this, but I'm virtually certain it can be used on a 100-ft 12AWG extension cord on a 20A residential circuit to paint his shed with no problems.
16 years ago, a couple of helpers and I painted my barn with a 5/8 hp Harbor Freight airless sprayer in a couple of days, running on 300 feet of 12AWG extension cords plugged into a 20A receptacle in my tractor garage! Even that $250 HF sprayer didn't complain. :laughing: