>a) I block or skip ads in media I consume

Skip is fine. Blocking with third party tools is a breach of contract as a consumer, but not fraud nor a crime.

>b) 1000 people block or skip ads in media they consume.

If they individually decide to do this, then it's 1000 times fine or 1000 instances of breach of contract. If they get together and do this collectively, or are instructed to do so by one person, it starts to encroach on civil conspiracy.

>c) I convince 1000 humans to play my songs every day and all of them listen to the ads

If you convince them to play the songs on the basis of the music, that's the very object of the contract.

If you convince them to do so on the basis of the ads, presumably you incentivize them with money if they listen to the song, then it's fraud. It's arguable of course, but if you are paying the listeners, then it obviously makes the value of the ads 0, you are knowingly selling something that has 0 value and charging a comission for that sale.

>d) I convince 1000 humans to play my songs every day and all of them to skip the ads

d) This is weird because your revenue would be 0 in this case. But arguably you would be benefitting from the service of music distribution without paying for it with the cost of serving ads along your music. It's a completely different situation than the one in the OP, it's more like piracy, less like fraud.

Again if by skip you mean a service provider interface, then that's fine, I'm assuming you mean block with ublock or some third party reverse engineered thing that's forbidden by ToS.

>e) I program 1000 bots to play my songs every day

e) Of course this is fraud, I think it's obvious to you and you are just positing this as part of the obvious end of the slippery slope, so it's not worth explaining why. But just as a teaser, it involves agreeing and breaching 1000 contracts and creating 1000 fake identities, so identity fraud at least!

>(b) (d) and (e) all have the same outcome for ad agencies, nobody hears the ads. If (e) is the only one that’s problematic, then we aren’t solving the problem by prosecuting (e).

Regardless of the specific case, in general there's many cases where regulation attacks only some scenarios which cause a damage, and that's fine. For example drunk driving, driving too fast, and blinking at the wrong moment all might have the same consequence, but we only regulate the first and the second.

>Similar vein to Matt Levine’s “everything is securities fraud” takes.

Haven't read that, but this is strictly not securities fraud, just fraud.