(1) Yes, one or two resubmittals as a site grows shouldn't prejudice it too much. On the other hand, the standards that a directory must meet in order to be considered "unique" are growing at least as fast as the ODP is -- and 99.99% of the wannabes won't cut it. I don't want to hold out hope, especially as ...
(2) I'd suggest a thought experiment:
Suppose for a moment that your website, your server, your computer, and all your backups were lost, and that you had developed amnesia.
What information would be lost from humanity? What goods and services would no longer be available to customers and accessable via the internet?
Write down all the answers. Now go back and look at the list. Cross out every word attempting to sell goods or services (that's advertising, and we tolerate it on sites, but we don't list sites because of it.)
What's left is the unique content.
If you need to wait until a brunette moment before completing the analysis, that's fine -- we can wait for your ODP submittals, we've got plenty to do in the meantime.