Here is something that might resolve this issue.
First, if possible, upgrade to the latest beta of GarageSale 8.1. If I recall correctly, it fixes some quirks with updating orders smart groups correctly when new orders arrive:
GarageSale 8.1 Beta 11 Released
Since this won’t cure problems with older orders, please start GarageSale with holding the Control key down, and select the “Rebuild Indexes” option from the Debug panel.
Then open the each of the Feedback smart groups and close them with the “OK” button. This should repopulate them from the database indexes you just re-build.
Any better now?