It looks like that text was pulled from a specific portion of the Kickstarter page; the people who can adjust that wording are currently not in the office. In the meantime while it may not be accurate for your specific pledge, the batches of pledgers are being managed by Goblinworks, and you will be added at the appropriate month in the Early Enrollment process.
Goblin Squad Member
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I think it's note-worthy to mention that "Head Start" is a totally different thing than "Invitation to Early Enrollment". I, too, have Head Start listed and it says that I get to join the game on the last phase of EE. But Invitation to Early Enrollment states I can join on the first month.
The benefit list simply contains all the possible benefits you can possibly get with your pledge level. Some might trump others. I think Head Start was a late addition to the Adventurer-level (35$?).
[Above ramblings are to say: It might not actually be a bug, but a feature.]
