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Have you never seen those highway billboards that rotate between three displays?

Advertisers will buy it because the seller can make the physical ad spot N times cheaper by showing N different ads during the day.

The question here isn't between static paper and e-ink.

It's between glowing LCD panels and e-ink.

Advertisers are already cycling their ads on LCD panels at bus stops, on the subway, etc.

Going to e-ink just makes the advertisement much dimmer, it can't handle video, and it becomes washed out. Why would avertisers ever prefer that?

Probably because they'd be cheaper and easier to see in direct sunlight.

Billboards are already digitized all over so I would expect any "We can make it N cheaper for N clients" pricing to already be done.