Auto File Uploading

I was wondering if there was an option that you can set for a certain file (ex: a .JPG image) to upload to the server like every hour or so.

For instance if I had a picture titled 'lol.JPG' on my computer I want it to update on my server as and refresh that image file with the current image on my computer.

Is that possible?

Yes. Use the Transfer Queue. Once the item is in the Transfer Queue, right-click on it and choose "Schedule" in the context menu.