Web forms will definitely be one for the future, but I think the learning curve is too steep to learn .Net and web forms in the short term, so we'll probably stick with windows forms for now.
I copied the exe onto the server as well as the DLL and was able to run the exe on another PC without installing anything. Is this a way of getting round deployment issues on users C drives?
If it's ok to have the Class Libraries on the server, is there an easy way of pointing the project at the dev version of the class library during development and then automatically using the live version of the class library when the exe goes live? Maybe by having a relative path to the class library rather than having to specify the server/path and dll name?