Can you imagine a realistic way around this issue?
Letting people communicate freely is a good thing in its own right, and fundamental to so many other good things we enjoy. Getting rid of a billboard for something I am never going to buy sounds great, but it kinda sucks for the person who actually is interested in the thing that billboard is advertising. Even if there were some type of advertising that provided no benefit to any part of society, the restriction on the freedom to communicate those advertisements is something that harms all of us.
Sometimes the part of building a better world that takes the most effort is recognizing where we already have.
I would argue that paid advertisement is a force distorting free speech. In a town square, if you can pay to have the loudest megaphone to speak over everyone else, soon everyone would either just shut up and leave or not be able to speak properly, leaving your voice the only voice in the conversation. Why should money be able to buy you that power?
and it also sucks for the billboard's location owner, who is drawing a revenue from it.
People who proclaim that doing XYZ to make the world better, is not really considering the entirety of the world - just their corner. To claim that it would make the world better, they must show evidence that it doesn't hurt somebody else (who just happens to be in a different tribe to the proposer).
why shouldn't it?
If somebody believes that their message is important enough to outbid everybody else, their message ought to be the one that is displayed.
And it’s kind of great for the (dozens, hundreds, thousand, millions) of people to pass by the location who don’t have some eye soar blocking their view.
Your argument is basically that there are some people who benefit from advertising—I promise you anyone antagonistic toward advertising has considered this fact.
The reality is that more often than not these messages are self serving and profit driven, many times borderline fraudulous in claims or questionable at best
the reality is that all messages, even those you think ought to be a grassroots message, are all self-serving. It's just self-serving for you as well as the message deliverer. And those "advertising" messages are self-serving, but not for you (or your tribe).
Therefore, this is just a thinly disguised way to try suppress the messages of those whose self-interest does not align with your own, rather than an altruistic reason.
and yet, the apparent disregard for the interests of those currently benefiting from advertising is dismissed as mere trifles, not worthy of compensation.
Policy suggestions should not be so one sided. I would always use the veil of ignorance, and ensure that any policy suggestion go through this retorical device.
It is not equally likely you will benefit from advertising as it is likely you will be harmed by advertising under a veil of ignorance scenario.
Sometimes (often?) people with a lot of money may not believe in speech but in suppressing speech. However, money should not allow for suppressing speech, for example by buying a giant megaphone and speaking over people.
By your logic paying people $500 to heckle at your political opponents rally is fine. It may be legally okay, but it is a moral hazard, and for a better society we should try to better distinguish between “free” speech and “bought and paid for” speech.