CKFinder - Clicking 'send it to the server' when uploading an image does nothing
The answer to this, as inspired by Nikit's comment, was to not use CKFinder at all.

CKFinder / CKEditor combination has to be one of the most frustrating experiences in all of Drupal, and it is the one thing I dread on each project. I have no idea why it has to be so complicated.

I kept CKFinder and used IMCE as suggested. The recipe works great; no complicated configuration; and is a much better module, in my opinion, for managing user images and file content.  I would suggest trying it as well if you find CKE and CKF as frustrating as I do.