GWT is pretty straight-forward and intuitive.
Especially with the release of UIBinder to allow GWT widgets to be laid out in XML and then coded-behind in Java.
So if you have used other Ajax or Flash design tools, or Silverlight, etc, GWT is very easy to learn.
The major hurdle, if not pitfall, is GWT RPC. The very reason you wish to use GWT is because of GWT async RPC. Otherwise, why not just rely on css to format your page?
GWT RPC is that element that allows your server to refresh data on your server without having to refresh the page. This is an absolute requirement for pages such as stock performance monitoring (or the current national and public debt of the US or the number of unborn babies aborted worldwide by the second).
GWT RPC takes some effort to understand but given a few hours, it should come all clear.
Above that, after putting in some effort to learn GWT RPC, you finally discover that you cannot use JSPs as the service component for RPC, unless ... I have an 8 part (I think) series on my blog on how to use JSP as the GWT RPC servicer. However, since you had not asked for answers but just issues, I shall desist from advertising my blog.
So. I very much believe that the worst roadblocks/pitfalls to using GWT is finding out how to properly deploy GWT async RPC and how to enable it to use JSP servicers.