No it won't, because there's no requirement that the result of `>` be True or False. It can return an object that then can participate in further expressions that "keep track" of what operations are done to the fields.

Not if you do the magic with getattr and comparison overrides. You actually need to do it on the metaclass because the Field as I wrote it isn't an instance but this works:

    from datetime import datetime

    class Filter():
        def __init__(self, name):
            self.name = name
        def __gt__(self, value):
            return {
                "field": self.name,
                "operator": ">",
                "value": value
            }

    class FieldMeta(type):
        def __getattr__(cls, name):
            return Filter(name)

    class Field(metaclass=FieldMeta):
        pass

    print(Field.end > datetime(2024, 1, 1))

This gives:

    {'field': 'end', 'operator': '>', 'value': datetime.datetime(2024, 1, 1, 0, 0)}

You can make python return arbitrary values for comparisons by overriding __gt__ (and lt, eq) on the first operand (which we control here since it is a Field class), it doesn't have to be a bool.

Edit:

You can even make a little adapter to use this with the current filter system if you really want to:

    from datetime import datetime

    class Filter():
        def __init__(self, name):
            self.name = name
        def __gt__(self, value):
            return {
                "field": self.name,
                "operator": "gt",
                "value": value
            }
        
        def __lt__(self, value):
            return {
                "field": self.name,
                "operator": "lt",
                "value": value
            }
        
        def __eq__(self, value):
            return {
                "field": self.name,
                "operator": "eq",
                "value": value
            }

    class FieldMeta(type):
        def __getattr__(cls, name):
            return Filter(name)

    class Field(metaclass=FieldMeta):
        pass

    def _(*args):
        kwargs = {}
        for arg in args:
            k = arg["field"] + "__" + arg["operator"]
            kwargs[k] = arg["value"]
        return kwargs

    def filter(**kwargs):
        for k, v in kwargs.items():
            print(f"{k} = {v}")

    filter(**_(Field.end > datetime(2024, 1, 1)))

This prints

end__gt = 2024-01-01 00:00:00

How would you model string comparisons with LIKE?