It really depends on the how your data is formatted. If you're keeping a simple local storage in text files, then it's just a matter of hitting up a server and checking if there is a new version of the file(s). If you're keeping things in local SQL storage, then you could use web services to ensure the local storage has the most up-to-date entries. I think that option is what you're looking for, and it would be really easy to write. However, if you're looking to update applications, then something like ClickOnce might be ideal.
In response to your edits
Basically, you have to structure your application to read all information from information files and give those files some meta-information like a "version number" or something like that. Then, you have an ASP.NET web service which has two functions: one is to get the latest version of the information files and the second is to download the updates needed to patch from one version to the current. So, the application would intermittently check with the server to see if there is a newer version than what they have. If there is a newer one, then it would ask the server for the patch files needed to get to the latest version. If you do this before the application actually starts (a la Firefox), the user doesn't even have to notice that the application is restarting.