We need to distribute documents to our partners on a USB key. I've been asked to develop a piece of software that will check if some documents have been updated on the server and proceed with the synchronization of files on the memory stick.
The software itself will also need to have an auto-update functionality in case we want to improve it in the future.
Where do you guys think I should start?
I'm assuming this is for Windows. C# would be an excellent choice, unless you can't be sure the user already has .Net installed. Otherwise I'd use Delphi, which can create native executables easily. The auto-update feature will be a pain no matter what language you use, given that a running EXE file can't replace itself. You can implement most of the program's functionality as a separate DLL which can be updated on the fly, but you're still SOL if you need to update the core EXE itself.