Oh Lordy just paid for privilege of upgrading to 22 but the thought of setting up everything again is making me feel queezy. One day it might be made a simple process like most other software. For now I’ll leaving it another day when I have time to write down all the extensions etc. Whoopie.
I keep templates, materials, components, and styles in their default AppData/Roaming/… folders and when a new version of SketchUp is released I simply copy those over to the new version’s equivalent folders. Extensions get installed from their source to make sure I have the most up to date versions. For extensions from Sketchucation I install the Sketchucation Plugin Store tool and then install my bundle from the previous version. Extensions from the Extension Warehouse get installed individually but I use this as an excuse to clean house and get rid of some extensions that I don’t use anyway. If you’ve been AR about keeping your extensions up to date, most of them could probably be copied from your previous version. Some extensions need to be installed using their installer to work. IF you haven’t kept your extensions up to date and don’t mind chasing loading errors, you could still copy them.
As for the workspace, I make a screen shot of the previous version and import that into the new version so I have a guide for where I need to put my toolbars.
Definitely one of these “could be improved in Sketchup” type of things but fortunately it only annoys once a year. 
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I know some folks have asked for some way to automatically copy extensions from an older version to a newer one. It doesn’t take much imagination to figure out that’s not a great idea. It would be nice if they’d implement a “bundles” thing in the EWH like Sketchucation has. There used to be such a thing before the last EWH overhaul.
Actually it hasn’t been too bad. The EW has a list of one’s downloaded extensions which rightly enough does highlight where some housework can be done. Thanks for the comments.