Here's a blast from the past... pre 4E software included the 'Master/E-Tools' debacle which was semi-successfully farmed out to Code Monkey Publishing. www.wizards.com/default.asp?x=dnd/dnd/20...
Though the E-Tools system failed to live up anyone's hope, the end product by Code Monkey is rumored to have been useable towards the end (when WotC let the licenses expire).
There are some amazing (read as fully functional) tools and products available through the OGL, some of which available for free or for a one-time purchase fee. Previously, it looks like, the OGL allowed some development of 3P software, but the current GSL does not.
At this point, well into the projected lifespan of 4E, is it possible to license the IP out to another company for the tools in question or will we be repeating this DDi v2, E-Tools v3, or Master Tools v3.5 with the launch of 5E down the road with a new in-house, out-sourced, or out-housed product?