All,
I have advised CUA-mode to support shift-selection-mode allowynd org-support-shift-select to work. The code is at:
https://github.com/mlf176f2/org-cua-dwim.el/blob/master/org-cua-dwim.el
Let me know if it works for you.
Reply to me directly if you have comments since I rarely check the org-mode digest.
Matt.