The Kickstarter Terms and Conditions expressly forbid this sort of fundraising. However, just by supporting us you are supporting our continued efforts to write about Perl (in either 5 or 6 flavors), to run Perltricks.com, and to support Perl.
For international pledgers, Christmas 2015 is probably not going to happen. We'd have to pay three times the shirt price to get DHL to rush them over.
For US domestic pledgers, we're going to work hard to do that. Once the campaign reaches its goal, we can get the size info and put the order into the t-shirt makers. From there it depends on how fast they can get the shirts to us. As with many Kickstarter projects, you'll see that the delivery of the physical items is out of our hands.
We don't know yet, but we have a secret list. Leave us a comment to nominate someone (or buy the reward to get your idea to the head of the queue). We want to get permission from whomever we portray so we might not be able to use your Heroes likeness.