The problem is that Roger is using Windows Media Center. The files previously created would probably have worked on a Boxee Box or WDTV Live player or using VLC, MPlayer, etc.

If using Windows with DirectShow you'll want to install a codec pack like either of these:

http://www.cccp-project.net/

http://www.codecguide.com/about_mega.htm

http://yatoshi.com/en/index.php?p=decoder

You should be able to use Handbrake's "preview" to test potential settings before committing to a full transcode.

I'd still start with MakeMKV which will dump all the DVD/BluRay menu cruft. Special features can sometimes be cool on disc-based releases, but animated menus and all that kind of stuff are just a total waste of time and only complicate navigation.

Which brings me to a side-note. IMO, DVD navigation/players were the worst implemented invention of the 90's. Everything from their remotes to disc layout sucks balls.