Hello nsblue, thanks for “rereading” and reconsidering this particular problem — and actually you were right both times:
(a) “WordPress can do permalinks” in different variations on the root-path construction of URL’s; and (b) you “haven’t seen anything in WordPress” allowing uploads to match the parent-path URL’s of this archival site. Neither have I seen any mention or means to do this within WP, and I’ve looked pretty hard at the relevant Codex items.
In describing your ‘batch load’ approach, I assume that you can create a directory of-choice on the server, and the resultant URL’s are consistent but still follow this root path. I need batch uploads to follow the parent path of the Page they belong to.
If native solutions are lacking in WP, we look to Plugins that purport to rewrite or redirect attachment links more flexibly. So far I have identified 5 such Plugins that have been kept updated and supported under current WP versions: Yoast SEO, Shortlinks by Pretty Links, Simple 301 Redirects, Redirection, Permalink Manager Lite.
If you know of others, please advise… and short of exhaustively testing them all, if anyone can offer a strong recommendation, it would be gladly accepted.
Thanks, scottie Free-Ass