Was it possible to use more then 1 coupon per order to get $40 off?
No.
-1
What's the benefit of that? Why not just do 2x $20 orders?
Manager issues...
It worked on a S&S card that didn't purchase any deals? Or on a S&S card that already used up its deals?
That
After some further research, it seems that my 2 accounts had been linked by S&S making them in technically the same account.... I stand corrected on this issue.
Did you have household coupon sharing enabled?