Knowing when to chop
Trichome color tells you the plant is ready. The forecast tells you whether you get to wait for that. Late in a short season, the forecast usually wins.
The trichome call
Start daily checks once pistils are 60 to 70 percent darkened. Most growers are aiming for mostly cloudy trichomes with a small amount of amber, but the right ratio depends on the effect you're after; more amber trends more sedating.
The weather call
A hard frost or several consecutive days of cold rain can force an early chop regardless of trichome color. Wet, cold colas sitting on the plant for more than a day or two late in the season is how bud rot starts.
Have a rain plan before you need one
Know how you'd bring an entire plant's worth of branches inside to finish drying if a surprise storm rolls in. Deciding that in the moment, in the rain, is worse than deciding it in September.
If you're drying with the roots on
Everything above still applies: the trichome call, the weather call, and the rain plan don't change. The only difference is that there's no chop. Instead of cutting the stalk at the soil line, you lift the whole plant out of its container with the root ball attached and hang it that way. Why we do it, and when you shouldn't, is in drying with the roots on, or cutting them off.
Two things worth sorting out before harvest day rather than during it:
Let the container dry down first. Stop watering a couple of days out. A saturated root ball is heavy, awkward to lift intact, and adds more moisture to the dry than you want, especially in a humid room.
Have the hanging point ready and know it will hold. A full root ball out of a 20-gallon container is real weight on a single point, and it needs to still be holding two weeks later. Knock the loose soil off outside, not in your drying space.