Hi Mike,
You can select multiple files for upload at once. When you browse to the location of the files you want to upload use Ctrl+click the files you want or Ctrl+a for Windows or Command+click/a for Mac. You should see the file names populated in the name line seperated by spaces. When you upload it should show the number of files and count them down as they finish uploading.
I do multiple picture files this way and it works well.
Hope that helps.
Dan