I agree with your comments.  Not having the functionality of changing the print order on Short Organizers is lame.  In light of the simplification brought about by the Jobs Act, it seems like a makeover of the Organizer is in order.  But for the health insurance page, it hasn't changed much in 15 years or more.

The "Tax Documents to Send to Preparer" is the most useful document in the Organizer module; a short sweet checklist.  Why hide it at the bottom?