Although there is no reason why you couldn't work from the smaller guides to the larger guides, I always work butt to tip.

Yes, you can tweak the guides after they are wrapped. Just use a smooth utensil or smooth thumbnail against the foot of the guide. Slow, but firm, pressure will move the guide as you like. Don't try to adjust the guides after color preserver is applied.

As you've probably figured, you will want to wrap all your guides before starting finish application.