50 feet is fine, 100 feet is pushing it.
For a 14-gauge cord carrying 10 amps, I’d keep it under 100 feet. 50 feet is totally safe and will work for almost anything.
The math is simple: voltage drop. At 10 amps on 14-gauge, you lose about 2% per 50 feet. Fine for lights and most tools. At 100 feet, that’s about 4% drop — some motors don’t love that, and you’ll notice dimmer lights. 14-gauge can handle 15 amps safely, but the longer the run, the more voltage you lose.
If you genuinely need 100+ feet, step up to 12-gauge. It’s a few bucks more and saves you from underpowered tools or a tripped breaker.
Don’t push your luck just to avoid buying a heavier cord.