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So only the ultra-rich can advertise through them?

Yeah, if we're to be allowing advertising like this then at least smaller businesses should be able to capitalize on it.

99% of billboards are commercial in nature, and are quite expensive even before heavy taxation.

Non-commercial speech is much better served by a human standing by the side of the road holding a placard.

what about a tax of incometimenumber * k ? (Oh wait, what does it mean to talk about a company or collective's income? What if you pay someone else to pay for the billboard? ok nevermind this is probably a terrible idea.)

Ha, as opposed to all the poor people using them now, to talk about what they had for lunch?

That's dangerously close to Citizen's United (with unlimited money buying "speech"). No, I prefer an outright ban to an economic hack.

The externalities you cite are not anything that causes a financial burden on society. Taxing them to recoup costs would be without basis.

Why do you value attention at $0?