Not sure that I understand you correctly ... I don't think you have to re-build any packages when you upgrade. The GD-2.30 that triggers the error on perl 5.8.7 is the very same GD-2.30 that produces no error on perl 5.8.8. It was built probably using perl 5.8.7, or perhaps perl 5.8.6, but I didn't re-build it when I installed perl 5.8.8.
(I don't think ActiveState have yet released a 5.8.8 build, and I don't know how long it will be before they do.)