I understand the challenge here. At the moment there isn’t much you could do other than:

1) adjusting the order’s shipping charge (as you are doing now)

or

2) adding a shipping credit line-item for that recipient. Such a product would have a negative price and you’d probably also set it up to be excluded from spending tables so that shipping discount does affect their shipping charge in the spending table.

Example – http://screencast.com/t/tKOhKzfcgN
and – http://screencast.com/t/gliRSS4Xt0

The feature request here will be to treat recipient shipping charges like order level shipping charges, allowing a manual override, ideally with a URL-like link that could be clicked to reset it back to the CMS calculated charge, again like is currently done for the main shipping charge on the Money tab of Order Entry.

In a future edition of CMS we do plan on allowing certain operations to be scheduled (processing back orders, future ships, authorizations/edc, releasing email confirmations, etc.) We’ll consider adding the running of specific reports to that list.

In the interim, you might look at the software called Visual CUT which can be used to schedule running Crystal reports including delivery of those reports to the intended recipients. http://www.milletsoftware.com/Visual_CUT.htm