Still have not sorted out the model orientation issue, but it seems that once you add some animations, everything rights itself. Not sure if this will cause problems further down the line, so I will continue to look for a solution.
Note: The missing head is intentional (not a bug/issue with export/import process).
No clue about materials, normals maps etc, but I can get from Blender to UDK with animations that I actually created. Poor, stiff, robotic animations, but I digress.
Happy enough with this for now.