I think you are correct, naive would have been a better word.

I was not trying to shame empathy, but I felt it would be cruel not to point out the difficulty of the situation. "Move fast and break things" does not apply when you have only one shot.

There are some situations (for example medical conditions) where a simple checklist approach can provide tremendous value. These are situations where most of the variables are fairly known, and none of the steps are likely to have bad consequences.

I don't think there is a good checklist unless someone has been in the exact position as the friend (same industry, same skill base, same visa, etc) and can come up with helpfull pointers.