90% of the time, when I want to add insurance, I forget.  Half the time I just ship it without extra insurance, half the time I cancel the label and create a duplicate label (which means my platform is not updated with the correct tracking #)

I do not want to use the insurance rules because 90% of the packages I add insurance to are priority mail - the insurance default assumes the package is not insured at all.  ($300 order, I would get $200 insurance).   So if it missed the insurance option being checked, I would overpay for insurance (which would be most of the time). Also If it's shipping within the same state, I do not add insurance, so the rules option would cost me too much in the long run.  (Also sometimes I spit a shipment into 2 boxes but do not know which items are in which, so I do not create a split order - I just use a duplicate label for the 2nd box - so the rule would over-charge me on those too). 

I tried the saved selections - creating an selection I called "priority insured" that way I have to choose between priority and priority with extra insurance - BUT saved selection does not save the insurance option being checked.

I am going to keep that saved selection "as a reminder" to check and enter my amount.  

Side note:  When we add insurance, it shows in a separate line below the postage cost.  It would be nice if when insurance is not checked - that line still shows but with "$0.00" amount, it would be a reminder in a location I always see just before clicking print label.