When we designed the new PDF export there was no requirement to be able to easily customize the PDF export UI to add new PDF export job request properties. i.e. to pass additional information from the user to the PDF export template. PDFExportJobRequestFactory wasn't designed to be overwritten, so PDFExportScriptService currently behaves as expected. From this PoV, this issue is a Won't Fix.
custom UI + overwrite PDFExportJobRequestFactory but install on farm and force a restart, as you suggested
custom UI + overwrite PDFExportScriptService, have you tried this? You need to set more properties in createRequest, based on the current HTTP request.
modify the PDF export to have some UI extension points, in the UI (PDF export form) and in the script triggering the job
I'm not fully convinced by the UI extensions because this is the first time I see this need to pass additional information from the end user to the PDF template.
This message was sent by Atlassian Jira (v9.3.0#930000-sha1:287aeb6)
If image attachments aren't displayed, see this article.