First, as an administrator I have a concern that I will face my stiffest opposition from parents (and maybe even from my immediate supervisors) as I incorporate Web 2.0 in the classrooms at our school. The most persuasive arguments I believe are the concepts of "half life of knowledge" and The Earth is Flat. The challenge is to distill this into a coherent explanation that will be presentable in 2 or 3 minutes and will be persuasive.
Another difficulty I am encountering is the speed of the current conversation. Sometime (maybe even most of the time) I feel like I can not keep up. If Web 2.0 is about reading and writing it is also about thinking and it is here that I falter. I am finding that it takes an incredible amount of time for me to assimilate and digest the information I am reading- perhaps because there are so many topics that are important and so much to learn. When I read blogs like Will's I am often inspired to enter the conversation but after a day of thinking there are already 20 plus new comments to read and think about.