Angie - I think it is hard to say what might influence your school administration/teachers. The "perfect score" requirement seems designed to allow almost no one to skip, but I have admit that it is a tad bit better than our schools...which currently seem to allow no one to skip/SSA (not with out of level testing, not with DYS-level IQ scores, not with high MAP test scores...).
You might want to go at it in a "how will you teach DS something that he doesn't already know this year?" angle if he doesn't get the skip. Truly, it seems difficult for schools to wrap their heads around students who are actually more than one full grade level ahead of their peers...some do, but they seem to be in the minority.
Something else to keep in mind (and perhaps aeh or someone else may have more details) - WJ may not allow DYS-level composite scores for very young kids. Since you are testing him for school, the limitations of the WJ (which someone else is probably better qualified to explain) may or may not be a concern. WJ may allow some high subtest scores. We ran into this when DS was about 4 and did testing for a local gifted program. His scores were very high, but we could not get complete composites and were told that there were issues with getting high composites for a young student on the WJ. He ended up taking the WIAT and did get DYS-level composite scores. Have you looked into having him take the WIAT? Of course, using testing that your school understands/uses is best.
Best of luck!