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This is just something that has crossed my mind lately, I might try to see if this will work but I would like other opinions and/or facts on this matter beforehand.

Yes, absolutely

Not sure, for me a painting is just a sigil with colors.
An hypersigil is supposed to have a fourth dimension that a painting lacks.
Some thoughts on hypersigils

1 painting can be a hypersigil, but a much better approach would be a series of paintings. If you look at salvador dalis landscapes they all tie together.

The 'Flower Of Life' performs very well as supposedly the Hyper-Sigil of hyper-sigils, and has been used pretty much the world over for thousands of years - but it can take a while for some to learn how to psychologically process fourth-dimensional representations in its hexagonal geometry, and headaches and even temporary visual distortions with objects gaining extra sides and so fourth can result if you overdo it. Mandalas though are other examples for the more cautious explorers favoring gradual development, and the 'optical-illusion' artworks of Escher are really good influences for inspiration too, perhaps.

Yes.

Sure anything more complicated than a standard sigil can be a hypersigil.

A symphony (mantrical), a painting or comic book (pictorial), the lyrics to nightman (word)

Hypersigils just blew my mind. The context of an Hypersigil is remarkable in that we already do it without realizing it. Think about the feedback loop of propaganda or media in general, where a series of ideas can change the shape of mass awareness. In these instances they may be unintended Hypersigils, perhaps in so being they can no longer be defined as a Hypersigil in that a concerted effort of will was not involved, and yet subconsciously they could be powered as such.

Very very interesting on the micro and macro scales. I will definitely have to give this more thought.