1.  Process images on Aperture.
2.  Use Arcurs keyword site for keywording right into meta data on Aperture
3.  export 10-12 images to desktop folder.  (10-12 seems to minimize pain if I get a picky reviewer)
4.  upload using Fetch (Mac FTP program) to each site.  I upload to individually to 10 sites.  I can do about 5 at a time. More than that the upload rates get too slow.
5.  Then go into each site to put in categories and approve and submit images.

Hi Bob

Mine is somewhat similar, but differs a lot at the end! I use Lightroom to keyword, using Arcurs keyword site as well. I then export all the images into another set of folders organized 2012>January, 2012>February etc. I put all the images I am going to upload for the month into that folder.

I have created a free account at Lightburner. This is a company/site that automatically distributes your files to all the main stock sites. Some sites are already set up in their system and you add your user/password, for the others, you can add a direct FTP account to distribute to them. I also use their resize function to reduce the size of images going to Shutterstock. So one FTP to Lightburner puts all the images on 20 or so agencies.

I then visit each agency at my leisure and decide whether to put all the images into their queue, or just do a few, as you are doing now. Generally I put them all in the queue as that seems to work OK for me.

Steve

PS without being too blatant with my advertizing, I wrote a long chapter about using Lightburner in my eBook about getting started in Stock!

I keep an open TextEdit file that contains the separated keywords for every picture I've done for the past several years.  When processing a new image, I go to the TextEdit file, do a search on the main term for the new image, and try to find something similar from my collection.  I copy and paste that similarly-themed set, but make a point to replace irrelevant ones and add new relevant terms for the new image. 

Do you use something like Lightroom or Aperture? I do the same thing but simply search in the database in Lightroom for a similar image (if I've taken one) and then sync the two images (old and new one) to update keywords, title and description.

Steve

On Mac as upload you can define in application Automator multiple uploads to xxxxx ftp-s
They are processed one by one but I find it is better than send one file simultaneously in you case 5 sites.