As mentioned I'm working with Mono and xsp. I now realize that in my working directory, MonoDevelop not only created web.config but also a bin directory which contains all of the dlls that I created and referenced in my project.
Setting xsp root directory to the path containing the web.config and ./bin enabled the http handler to be found and allowed me to finally access my web service and
http://localhost:8080/ServiceStack/metadata
In this scenario I did not need my dlls to be in /bin but in the project's bin
I had also overlooked the call to HelloAppHost().Init()
Bit of a learning curve... but I'm looking forward to using ServiceStack.
Thank you @mythz and @Mr.Young