If we're talking D&D e-tools as one of the original problems here, one of the main setbacks in that project (if I remember correctly) was Hasbro's licencing of D&D computer games to Atari, which in turn sold out certain rights the e-tools program needed from under WotC without them knowing about it until their people had a good part of the software written.
Originally e-tools was supposed to have a really nice mapping feature with animated 3d monster models. The terms of the licence sold to Atari for them to publish Neverwinter Nights said that only Atari were allowed to make a D&D "computer game", and the 3d map was seen as being far closer to a computer game than a tool. Hasbro saw the money and went for it, WotC found out way too late that their parent company had sold away half the rights they needed to retain for themselves.
I suspect Hasbro would have sold the rights anyway, even if someone at Wizards had pointed it out - from their point of view the NWN deal was bound to net far more income than a computer program aimed at a small group of pencil-and-paper gaming nerds.
Disclaimer: At least, thats what I recall being reported at the time.