This is almost always a good thing, as the underlying tradeoffs of a policy are more likely to come into focus once you have examples of real people on all sides of a real controversy, with concrete gains and losses.
What you'll find is that there's typically some very broad law on the books, e.g. banning vague categories of anti-competitive behavior. Then the lower courts will hear a bunch of cases of varying similarity, a few get appealed here and there, and you eventually end up with stronger guidance as to a more specific issue.
I don't think this has anything to do with free speech, but more about fair business practices.
I think there are problems with casting it this way. You can get in trouble for making false claims in ads.