Google is going to be making this easier in the future. There is a good indication that the Doc List will be renamed "Google Drive" soon. Google it for more information. In the meantime, Cloud Sherpas (a reputable company) has developed a bulk file uploader which has some great reviews in the apps marketplace. I am not currently an employee of Cloud Sherpas and have not used their product. But if I had a similar problem, I would try their product based on their reputation.
What is the best way to upload a lot of files to Google Docs?
