Hi Jack and Patrick,
I just did a clean install of SIMA/ROIBuddy in a fresh Anaconda environment using Christophe Gohlke's pre-built windows python wheels (
http://www.lfd.uci.edu/~gohlke/pythonlibs/) and it worked OK still.
I downloaded the wheel files (all Python 2.7) for shapely, pyqt, pyqwt, guidata, and guiqwt, and then pip installed shapely.whl, sima, pyqt.whl, pyqwt.whl, guidata.whl, guiqwt.whl, and roibuddy.
I've also seen the issue where the exe doesn't actually run, we'll need to look in to that more, but roi_buddy.py in <site-packages>/ROIBuddy should work.
Let us know if you have any additional issues.
Jeff