Question: Why transfer him at night in bad weather? That and given his past why not have him cuffed to the gurney and have armed guards there regardless of his comatose state?
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Answer: The best in-universe answer I could give you to your first question is that Michael just happened to be scheduled to be transferred at night and the weather ended up being crummy. I've been transferred between hospitals at night before. (Albeit, I'm not a homicidal maniac.) But honestly, the real answer is simply... "because movie." It's a horror movie - it's just more dramatic for the scene to be set at night during lousy weather. It wouldn't be nearly as effective a scene if it was during the day in nice weather. A dark, stormy night is sort-of a convention of the genre. As for the second question, he was severely burned in a fire and has been in a comatose state for years and years. Realistically, it was safe to assume he wouldn't wake up, and even if he did, a normal person's muscles would have likely softened into jelly in the meantime. They assumed they'd be safe... but they were wrong.
TedStixon
The question would be why did the characters transfer him at night in bad weather, not why did the film makers set it up like that. The viewer may thought he or she missed the in-film explanation or was looking for someone with expertise in transferring patients to provide an answer. And again, was there any in-film explanation given or persons with experience in transporting patients like Michael (albeit without supernatural powers). Pointing out the caveat of character's actions isn't realistic because it was scripted that way is fine, but pointing out that a movie is a movie isn't a valid answer (or correction).
Bishop73
I did amend my answer slightly before I saw your response. I really don't think my initial answer was that invalid though. That's honestly the truth - it was done that way for dramatic purposes, and any other answer would be pure speculation.
TedStixon
If no in-film explanation is given, speculation is OK as long as it aligns with something that would happen in real life (although I would suggest saying it's speculation). Sometimes people do ask question about why film makers would do something, and an answer like "to make it more dramatic" would be acceptable.
Bishop73