"Would site anonymization to "delete" the offending DICOM header allow for the upload?":
I hesitate to say "unconditionally yes" as there are a lot of subtleties with anonymization, including interactions with the various upload paths. That said, roughly, yes I would expect that to work. It certainly did work for me doing a quick test with site anon + compressed uploader. YMMV
"I don't think there is a "truncate" Dicom Edit function, but that would be nice.."
True, but there is a substring method and a match method. I'm not sure how resilient the substring method is to values that are smaller than the endpoint of the substring indices, but if that doesn't cause a problem, you could probably "make" a truncate method using substring. If that doesn't work, match probably would, but I'm no regex expert :).
Thanks,
Charlie