Stick to 50 feet for a 16-gauge cord with a 10-amp tool.
50 feet. That’s the safe max before voltage drop starts robbing your tool of power and potentially damaging the motor.
Voltage drop is real. A 16-gauge cord has resistance. At 10 amps, every 50 feet drops about 3-4% of voltage (assuming 120V supply). Go to 100 feet and you’re looking at 7-8% drop, which is enough to make a saw blade spin slower, overheat the motor, and void warranties. Most tool manufacturers recommend keeping drop under 5%.
If you need more than 50 feet, step up to 14-gauge (good to 75-100 ft) or 12-gauge (100+ ft). Don’t be the guy dragging a 100-foot 16-gauge cord to a circular saw and wondering why it smells like burnt copper.