I can be considered a High Level user of WP and s2member, meaning I’m not a programmer, so please take my comment with a grain of salt… but I have found Courseware to be buggy. Last October or so I tried running Courseware and had numerous problems with CSS, and there were security problems as well. It seems that even with s2member installed, something that was supposed to be secured still got through the cracks. I don’t believe that the failure was on the part of s2member, but rather Courseware.
Courseware also seemed to open up the site to receive comments, even when those comments were completely deactivated. Deactivated through the individual pages and posts, and within Dashboard > Settings > Discussion.
Courseware proved to be too much maintenance for me, so I conceded and went with Moodle.
Moodle is overly complex, but it’s secure compared to Courseware. And Moodle is updated on a very regular basis.