I've been using Webmatrix/WebPages/Razor for a while now and like it. It's been a while since I used Classic ASP, but WebPages to me feels like a true successor to classic asp and what ASP.net should have been from the start. I'm actually moving most of my smaller sites to the WebPages framework from WebForms. Here are some things I've encountered.
I'm not sure if this is a gotcha or not, but I thought I would mention that with WebPages the scope of your variables may behave differently. I know a lot of Classic ASP sites that used to use include files to run snippets of code. Many of them depended on global variables set in the parent document. In WebPages, if you use RenderPage or Helpers to replace includes they run mostly outside of the Parent's scope. If you used Server.Execute instead of includes then you might not notice much difference, but if you did use includes and lots of global variables you may notice it.
Another possible gotcha is in ClassicASP <%=%> doesn't encode output, but in WebPages the Razor syntax @ encodes output by default.
Another thing to consider is using C# vs VB.net with Webpages. Although vb.net works you'll find that most samples, tutorials and people in forums use C#.
Finally something that bothers me is that it is named the "webpages" framework. I've found it hard to do a good Google search using the term "webpages". Even "asp.net webpages" brings back mostly webform results. I have more success using "webmatrix" or "razor".