Fill out the document with any additional detail I might have missed for each option
Once each of the options is clear, we eliminate any options that could lead us to an incorrect or misleading type hint (e.g. most likely option 1 here, maybe others)
Evaluate user experience in each case, what happens to the person that tries this, are they helped by what happens (we can give each a rating out of 5 perhaps)
Evaluate how easy life will be for type checker developers (again, rating out of 5)
I'm hoping that perhaps we can agree on the ratings quite simply, but if not we could vote for them somehow. Also if there are metrics I've missed that would be useful I can add to this.
I would suggest we do the following:
I'm hoping that perhaps we can agree on the ratings quite simply, but if not we could vote for them somehow. Also if there are metrics I've missed that would be useful I can add to this.