This is going to be a bit shorter than my last wall of words on the subject of D&D Insider.
I just read a piece by Timothy Burke where he describes the perplexity experienced when hunting through the Wizards of the Coast website a few days after the new system was launched, looking for the Insider tools that were so massively hyped as a key element of the game during the year or so before release. I experienced the same bewilderment myself at the time, although with less success in my hunt for answers on the official site. Tim found the FAQ with an explanation: I had been stymied by Wizards' decision to try everything short of removing the lightbulb and sticking up the famous "Beware of the Leopard" sign on the door. Instead, I'd turned to the rest of the web for information on Wizards' own product.
I remember a description from my postgrad course about the stages of crisis at which companies lie to themselves and mislead or deceive their customers. This one really fits the pattern described.
Tim (I have referred to his blog before, and am never am never sure whether to use the full or informal forms of the name of someone I don't know. But Tim seems more .. wizardy) believes that the prognosis is poor for the online tools suite. In a classic example of wood and trees, I'd not thought about that, despite being in the position of working in the world of software development (sort of). I imagine it depends where Hasbro see the D&D brand going in future. If they believe that it has serious upside, especially in the online marketplace, then they may bite the bullet and throw the necessary money at the project. If they see it as a niche product - a cash cow with gradually fading prospects to whom they gave a few million for a chance to pep up the product range - then a delay of many months would sem potentially fatal. Given Wizards' history with what they unfortunately tended to call "eTools" in the past, my guess is that they'd be more likely to scavenge some of the easier-to-support elements like the online rulebooks and go with those in some very limited fashion.
From my experience in content delivery, I'd not be surprised if that area was one of the real stumbling blocks: there is an awful lot of content to be converted for the rulebooks, and massively more (much of the older stuff unavailable in useful electronic formats) for the bundled magazines. It's prosaic, and so tends toget overlooked until it is realised that there are six weeks to launch and several hundred content issues outstanding.
If asked to bet, I'd say that the bulk of the functionality will be released, much of it during this financial year. But it'll be stupendously buggy in places, will provoke a lot of bad-feeling about reliability during the beta period, and price afterwards, and (I still believe) will provide stimulus to the open-source softwaer movement to provide something better and free.