I doubt I will ever go "paperless" as I love being able to spread papers out and work on them side by side and rearrange them. However, I also need to have digital copies of these documents both for my own research and to share with my cousins.
Today I spent about an hour digitizing all of these documents. The actual scanning only took about 25 minutes with my ScanSnap IX500. It would have been faster if the papers hadn't needed staples removed. After that, I spent another 35 minutes briefly looking at each set so I could label the files. Now, I've saved the files to DropBox and they are ready to be shared!
By the way, this is my craft/genealogy room. We moved into our new house two years ago, but I still usually use my kitchen table for my work. Within the next few months, I'd like to hang up photos, maps, etc, and really start using this as my work room.