It's been a long time coming but I've found a great tool to help with uploading multiple sets of photos to the gallery in an automated way.

The first thing you'll need to do is download the gallery client tool in the link below then install it on your local machine by running it:

http://www.fooriders.com/software/ChiwisCSGalleryManager_2007_beta_2.msi

Once it's installed, click on "Manage Connections" and you'll get a popup to configure the settings for connecting to the fooriders gallery. Fill it in like this, but with your own user name and password:

The text for "Gallery Service" above is: http://fooriders.com/CS/photos/ChiwisGalleryService.asmx

Hit the Save button when you're done then Close. You should now be able to connect to the site by using the drop-down menu for "Connect to...". I've found that the app is easiest to use when it's maximized so you might want to do that to make sure you can see all the content. Once logged in, you'll see your local folders on the left side of the app and the fooriders gallery contents on the right side. In the image below, you can see the contents of Winston's gallery.

Select your gallery from the dropdown menu on the right side and it will show you all the albums you have in your gallery. Click the checkbox next to the album name that you want to upload to, then select the files you want to upload by choosing the thumbnails of the appropriate folder on the left side then clicking on "Add to queue". Note that you can do a Control-A to select all the files in a selected folder. In the image below you can see that I've got two files queued for upload to my "Bikes" album in my gallery.

 Once you've got all the files selected for uploading, just click on the Upload button to initiate uploading. One by one the photos will get uploaded. To avoid LOOOOONG uploads, it's best to make sure you've already resized the photos in your local folder to a max of 600kb or so per photo. If you don't have a tool to resize batches of photos, download Microsoft's "Image Resizer" Powertoy at:

http://www.microsoft.com/windowsxp/downloads/powertoys/xppowertoys.mspx

After you've installed the Image Resizer Powertoy, you can use Explorer to right-click on one or more photos to resize them. I suggest a custom size of 1280x1024 or so.

If everything goes smoothly, you should be able to go to the "Photos" section of the site and find all your uploaded photos in whatever album you uploaded to. All your photos are now all available for including inside your forum posts by click on the "Content Selector" icon when you're creating a forum post. That icon looks like this:

Hopefully that explains the process well enough to get you started. Post any questions here and I'll try to answer them.