I suspect the dialog you refer to is a standard dialog used by the python distutils (and/or elsewhere). Probably could be changed but then the users who are used to the default behaviour (it is not only used in weeWX) will complain due to a non-standard dialog. I think the lesson is that if you have customised your weeWX installation (as I have) you need to carefully navigate through any upgrades (as I do). If you make a mistake you may end up with something that is different to your pre-upgrade situation, but as part of the upgrade weeWX should retain copies of the pre-upgraded files, albeit with a slightly different (includes a timestamp) file name.
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