Microsoft should show always show all the privacy options to users and they should explain the pros and cons for each setting. Explain them that Cortana won't work anymore if they don't enable something, but also explain them that the NSA will be getting all their keystrokes if they do enable it.
Here in Europe we are not protected by US law against the NSA (although there seem to be all sorts of loop holes in the US too), so we should expect here that all the data that Microsoft collects is directly sent to the NSA. It's unacceptable that they offer a one click 'share everything with the NSA'-button when there is no matching 'keep all my data private'-button.
But the absolute worst thing ever is that they seem to throw away old settings after some updates. So even when I make sure that my parents computers are properly protected against Microsoft or even the NSA spying on them, I still can't expect that they will stay that way in the future.