> For news, consider things like the Chinese wall [1] between news and ad sales
Literally the second line of the two lines of the linked section talks about the (increasingly common) cases of it being breached, a natural consequence of increasing ad-blocker usage. Also, everything in the example you're giving relies on old distribution methods, not "news". There's no longer a line between news and "random website who publishes information about events", and I'm not sure how anyone who hasn't been living under a rock for the last 15 years could be naive enough to think otherwise. For God's sake, Buzzfeed was a Pulitzer Prize finalist a year or two ago!
> For books, I'm not even sure what you mean. Book publishers sell books that they think will do well and, mostly, that reflect well on them. You can't just walk into Random House with a credit card and say, "Here's my manuscript, please put it in book stores nationwide."
Amazon is the largest bookseller in the country IINM, and you can very much give them a credit card and start selling your books nationwide. Again, you're confusing increasingly-unpopular (for market reasons) distribution methods with types of media.
The very existence of advertorials is a refutation of the notion that there's any principled way to legally distinguish between advertising and other forms of information, even less so one that wouldn't be riven with loopholes (cf limits on campaign spending and Super PACs' technically-not-for-the-candidates' spending).
> Personally, I'd just ban all advertising.
You seem to be confident that you have a definition of the word advertising that would be robust enough to implement this without enough collateral damage that it wouldn't be trivially unconstitutional. What is your rough proposal for what that definition would be?
FWIW, I generally agree with you that advertising is a collective-action/net-loss problem, but I think you may be falling into the classic trap of "this thing is bad, we should just wish for it to disappear and hold all else equal".