When testing the various operating systems and browsers for image uploading, I noticed that in particular Internet Explorer prior to IE10 .. sucked. IF you're going to use IE at all, I recommend at least IE10. If you can't, then use another browser.
The rest of this thread will focus on some of the various ways that things fail, more for Robin's sake than anything. I'm hoping Robin's official position will be "Use IE10+ or another browser". I don't know how much of this is worth fixing - only his web server stats can say.
I'll occasionally come back to edit this top post with a 1 line status to avoid needing to wade through the rest of it.
All testing is being done using Parallels on Mac, using official Windows images downloaded from http://modern.ie . The only software add-ons I'm doing beyond this are Charles Proxy, http://charlesproxy.com, in order to man-in-the-middle the SSL API calls and report what the Pinside server is reporting to IE.
IE6 on XP: Does not connect.
IE8 on XP: Does not connect.
IE8 on Win7: Missing visual elements. Bad response to image uploads.
IE9 on Win7: Bad response to image uploads.
IE10 on Win7: Works.
IE11 on Win7: Works.
IE10 on Win8: Works
IE11 on Win8.1: Works