Looking at my dashboard, it says that my sites are running version 4.9.9 and that it is the latest version.

After a conversation with support, it seems that the upgrade process to get to a 5.X branch is this:
1. Turn of core updates.
2. Manually update the site.
3. Every 59 days chat with support to get another 60 days so that core updates won't turn back on and revert the site back to 4.9.9.

If a perfect world, the updater will magically update the site to 5.1 and everything will work perfectly forever. I understand that this is hard and you've got a team of people figuring it out but can we get a message at least? Maybe something like this:

Version 4.9.9
Status WordPress is up to date.*
*Automatic updates to the 5.X branch are currently being worked on, for more information please go here: <link to more information>.

Thanks.