Will Drupal 6 be left in a secure state after it becomes unsupported? I created a custom database interface using Drupal 6 + Views + CCK that works really well for my company and recently I had to migrate it to another server.

I thought "Hey, why not install Drupal 7 and then dump the database in it: then I can upgrade Drupal to the latest version while we migrate!?"

That turned out to be a bad idea. Drupal 7 doesn't seem to have the slightest clue what to do with the DB info I gave it. And the upgrade guide looks very time consuming to me, right now.

So my question is: will Drupal 6 be left in a secure state after it becomes unsupported? Or will the platform become deprecated and vulnerable forcing an even more massive upgrade on me?
Once Drupal 8 comes out, Drupal 6 will be marked "end of life": the Drupal security team will stop working on it and official security releases won't come out for it. If any new vulnerabilities come out, you'll have to patch it yourself. So it's really in your benefit to upgrade at that point.

But upgrade paths for Drupal are from the previous version to the current version: that is, an upgrade path is provided from the last release of Drupal 6 to Drupal 7, and an upgrade path will be provided from Drupal 7 to Drupal 8.

There won't be an upgrade path for Drupal 6 to Drupal 8: if you don't want to rebuild your site from scratch when Drupal 8 comes out, you'll need to first upgrade your Drupal 6 site to Drupal 7, then upgrade to Drupal 8.

So, it really comes down to economics and long term planning. Drupal 6 will be supported until Drupal 8, but when Drupal 8 comes out in a couple of years, will you have an opportunity to rewrite the site? If not, you should plan to upgrade to Drupal 7 at some point in the future.