I work between two servers, and I use one for development and the other for deployment. It’s very easy because I can tell the development one to use the database of the deployment sometimes. What I can't do is upload the images to a third service so both the sites will see the same images. Do you know any workflow in which this is possible? Are there any modules that allow you to upload images to an external service?
In my one of my setups I have a main server and a backup server. They are separate small virtual machines on different physical boxes. The entire Drupal install including file uploads is copied over from the main server to the backup server using rsync.
Rsync is an excellent command line *nix tool for copying, syncing files both locally and remotely. There are many configurations you can use. You can then configure a cron job to run it every so often. Here is one of the hundreds of threads
In your case you could just rsync over the /sites/default/files folder. Just one solution to your problem, but there are many.