There are too many holes in J.K.'s mythology.
As for portraits, I think they can be brought up-to-date, and perhaps even grow as "people" by observing what they can from their frames, and interacting with live people (and even other portraits in their building) ... but I have a hard time reckoning that their essence isn't set when they are painted.
If Dumbledore were painted before his sister died, I don't think the portrait Dumbledore would be as psyche-damaged as the real Dumbledore, even if the portrait one learned of the circumstances.
Hey, and what happens if ... as with many famous people ... more than one portrait is painted, and at different stages of life? Under my theory, the portraits would each be very different "people."
And yeah, witches celebrating Christmas is just odd. But I think it's more a matter of them being Brits than being witchfolk.
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