Go to Preferences->Add your own column, create a text column with multiple entries, like tags, and enter as many titles as you like into it. Create another of type enumeration and fill it with your publication types.
And I dont see how putting the toc into the comments field fails to achieve the "goal" of calibre. If you want some data to be searchable, it has to be present somewhere, either in a custom column or the comments field. Someday, I will add full text search to calibre, at which time, even this requirement will no longer exist.
The title is most definitely not going to become a multiple valued field.
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