Update: I took a different tack this time. Instead of asking them to fix the download so there's no DRM, I just asked if there were any updates. (One of my books was missing the maps in the original version, which was a convenient "hook" to build that question around.)
After that, they updated all but one of my Tor books to new versions with no DRM and KF8, as well as a number of other titles on my account to be KF8. (The exception is
The Stars Like Dust, which I own an ancient Topaz copy of. At some point I'll ask them to change to the new edition, but since it's technically a different edition I understand why it's not quite so simple.)
Now, why they didn't just let me automatically update from the web as you said I should have been able to, I don't know. But all's well now.