Loadout timing
Pilgrammed loadout guide
This page helps with the real question: when does switching into a greedier or stronger build actually improve your results instead of slowing your progression.
Before you switch
Your current build is holding you back more than your route execution is.
The next gear layer gives you a real survivability, damage, or utility advantage instead of only looking flashy.
You understand what the harder loadout changes instead of switching only because your current route feels boring.
You are not giving up a stable progression route for a fragile option that you still cannot support well.