So I saw this glee canon awhile ago about how Burt bought Kurt his Marc Jacobs bag to match his warblers outfit and I think Glee, Actually confirmed this, or at least the fact that the bag was bought specifically for the warblers outfit. So pre-dalton, kurt carried around this brown bag. The first time we see kurt with his marc Jacobs bag is the first time we see him in his warblers uniform. In Glee, Actually, Kurt never met Blaine or visited the warblers in Artie’s dream, and we see Kurt carrying around his brown bag. It’s all in the details.
With the weird timing of the release of the show and the story he's telling, part of me really wonders if D and Ryan organised it together so him coming out would happen as they were doing press for the show? I mean, it gives him extra time to organise everything, get certain people out of his life, sell the PR house, get out of the contract etc PLUS the benefit of the show getting some extra buzz. The thought crossed my mind, and I feel like it makes sense.