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 http://website.com/lol.JPG 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.
Regards,
-Mat