Watched a buddy make that exact call on his mountain bike last season. He threw a new chain on a worn cassette and it slipped so bad on the first climb he nearly ate it. The old rule is if your chain is stretched past a certain point, the cassette teeth are already hooked and won't play nice with a fresh chain. You need a chain checker tool, the cheap kind works. If it drops all the way in, you're usually too late and the whole drivetrain is shot.

@shane244 yeah, life changed my mind on that one.

Chill out, it's just a writing prompt not a life choice. Cameron's right that it changes with your mood, so maybe stop making it a big deal. Pick the one that works for you and just write something.