A good checklist should be diagnostic. This means that it can find problems if you have any.
However, the checklist also needs to find those problems fast.
This is where the notion of failing fast comes in, which has become a tantrum in lean business literature.
Failing fast means getting feedback fast.
And the faster you get feedback, the faster you can correct course if you happen to walk on the wrong path.
Therefore, order your checklist items so that those items that are likely to fail comes early.
This will minimize the time you spend checking boxes and maximize the value you get from fixing the problem early. Especially when you run through the same checklist many times.
References
Scriven, M. (2000). The logic and methodology of checklists.