A bit late to the party, but I just wanted to say that this checklist was extremely helpful for me. We've started a Tableau User Group here in Lexington, and our first meetup was on January 10. The checklist really made everything easier to organize, and brought to light some things I hadn't thought about despite how obvious they were (e.g., rotating slideshow prior to the start of the meetup, spin-offs (we have a co-leader that's heading up our Data+Women user group!), etc.). Thank you for taking the time to put this together.
I'm really glad you enjoyed it! Thank you for the comment.
I'm collecting all the links I can find about creating user groups into an infographic - would you mind if I included your post?