Just letting everyone know, I have been given the go ahead to develop a plugin that will allow a user to upload files to the s2member-files secure directory from within a post. I haven't started working on it yet, but I plan to have it finished by the end of the weekend.
I'm going to submit it to the WordPress plugin repo and will notify everyone on this thread when it is ready.
If you have any suggestions or thoughts, I welcome them.
Lew