Yes, the skyway should reopen. While the deaths of 23 people is horrifying and tragic, this was over forty years ago. This has been more than enough time for Disneyland to have a better system in place with better technology. Train crashes happen almost daily and this doesn't stop commuters from using them.
The skyway is possibly less dangerous than it was, but it is still very dangerous. It needs to be safe and upgraded before it could be reopened. There is way too much traffic for the skyway to be opened. There is more traffic now than there ever has been and an accident could be more deadly.
Helicopters are far more dangerous than other forms of air transportation. In addition to that, they are also carbon-guzzling vehicles and would have a negative impact on the local environment, While the view from the sky might be impressive and magical for children, Disneyland should explore other options for recreating the experience that doesn't come with so many downsides.
While the idea of arriving to Disneyland by helicopter seems like something out of a fairytale, it also seems to be an unnecessary risk considering it has already cost the lives of 23 people. One skyway would take up a lot of room that could be used for another attraction.