Enclose
cusSet.Tables("Customer").Rows(accountIndex).Item("ExpirationDate") in a CDate, and see if that solves the issue. In some cases, it may not implicitly convert an object in an equation when you're working with Data, and so it may just stay as an object.
It should be like:
If CDate(cusSet.Tables("Customer").Rows(accountIndex).Item("ExpirationDate")) < Date.Today Then
Try that, and see if it works. Could be overly simple, and perhaps you've tried it before, but it might work.