I think the best way to adjust to change, is dive head-first in.... buy a chromebook, and ONLY let yourself use that machine for 2 weeks... write down anything you needed off your old machine, or that you couldn't figure out.... then after 2 weeks, grab those things off your old machine, and you should be a ready-to-go Chromebook user.
I think the worst way to change, is to sit their with 2 machines open.