Hi Chance,
I never buy less than a 14 gauge wire. I know that it drops voltage/amperage a little with a 100 foot run, but I'm not running large enough a motor to be concerned.
I think my longest 12 gauge is 75 feet.
Some years back I purchased a corded trimmer and an extension cord for my wife's brother-in-law. It was a thank you gift for inviting us to his beach house. Reading the recommended cord gauge for the length B.I.L. would need, the cord cost more than the trimmer.
Our eldest loves to decorate the yard for Christmas.
HA! Last year his Christmas present was a new 100' cord.
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