I post two sets of articles written by random people every month.

Link 1 - http://www.dozwm.net/shirley.html
Link 2 - http://www.dozwm.net/current.html

Plus I add "printable versions" on each page (link to the word document)

I then archive them here:http://www.dozwm.net/Archive.html
For this year - http://www.dozwm.net/2012Archive.html

Is there some crafty way to automate this whole process? I'm getting tired of this.

Why not start an S-Drive Stream for each of the different places you post at. This would then allow you to post it and forget it as it would automatically paginate them for you so you don't have to actually archive them. Something to look into maybe. Check out the Stream and see how it works it's pretty easy to use and might just do the trick for you. You may need multiple accounts for this though or maybe you can host more than one on an account, not sure how that all works.