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Something like first creating listener with /filewatch <name> <file> and then using On 1:FILECHANGE:name:commands

Yes, a /filewatch would be required. mIRC only parses events when something triggers them, it does not create triggers out of events.

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It would likely check for change the same way that Initialization Warning checks, by looking only at timestamp date, and not filesize or contents.

Yes, it would use exactly the same method since it would be using the same routines.

The use of a CRC check has been discussed before but it would not be practical. If someone has a large number of scripts loaded, this would result in a freeze every time mIRC had to scan all loaded scripts, eg. at startup, whenever you edited a script, or during file change notifications, since a CRC check would take time to perform. A file time check, on the other hand, is instant and, although there may be some outliers, is generally satisfactory.