The courts already distinguish "commercial speech" as a class of speech. Would we prevent all forms of commercial speech? What about a waiter asking you "would you like to try a rosé with that dish? It pairs very well together." Is that "advertising" that would need to be outlawed?
What about giving out free samples? Is that advertising, and thus should be illegal?
What about putting a sign up on your business that says the business name? Is that advertising?
I hate advertising and propaganda. But the hard part IMO is drawing the line. Where's the line?
Being unable to tell when something is "advertising" forces everyone to think twice before hawking their wares, which is exactly what we want if we intend to kill ads. The chilling effect is precisely the intention.
It’s the engineer’s curse to believe that airtight laws are automatically better, or that justice springs from mechanistic certainty. The world is fundamentally messy, and the sooner we accept its arbitrariness, the sooner we can get to an advertising-free world.
That's why we have judges and lawyers, so that the outcome can be decided as a communal process instead of just one person deciding what is punishable - even if the person is the developer building the automated justice dispenser and they'll be not around when the decision is taken, it would still be made by the whims of a single enforcer.