I think we may have hit the nail on the head. I was talking to one of my friends who was getting a warning to upgrade firefox. He waned to bypass the message and I told him that the best way to do that was to upgrade. He said he did not want to upgrade (he had a very old version of firefox) and when I asked why, his reply was "I am of the mentality that if it isn't broke, don't fix it". To be frank, I was shocked at the lack of understanding and unwillingness to upgrade.

Here are a few examples of others with the same attitude:
http://support.mozilla.org/en-US/questions/925863#answer-327842
http://support.mozilla.org/en-US/questions/825553

A quick search on google will show many others who have the same mentality. Some even complain that they can not entirely disable updates. I think this is one major issue that wordpress might want to address. However, is it really up to wordpress or is it up to the end user. If wordpress are targeting new users, I think this mentality will need to be addressed otherwise the users will experience issues and naturally blame wordpress, plugins or their theme.

While professionals such as ourselves know what needs to be done, many new users do not and they expect wordpress to look after its self. We have a monthly checklist for all of our sites and the sites we manage which includes every corner of website maintenance you can imagine. This ensures that the websites are all in the best possible state.