I think a lot of people overestimate how hard it is to stay hidden for small jobs.
Furthermore there is a lack of imagination here:
- work from a hacked account (I've seen gmail accounts that have been "shared" with an attacker for long enough to let the attacker having conversations with their bank, i.e. attacker used the account but stayed hidden until the bank called to verify details.)
- VPNs exist.
- Russia exist.
- nasty images can be embedded into details of innocent high resolution photos.
- very soon they'll have to scan pdfs, pdf attachments and zip files otherwise this is just a joke.
- at this time it becomes even easier to frame someone
- etc
Remember, the goal is probably not to get someone convicted, just to mess up their lives by getting business contacts, family and neighbors to wonder if they were really innocent or if they just got off the hook.
That said, the bigger problem with having a secret database of objects to scan for is that it is secret: anything can go into it, allowing all kinds of fishing expeditions.
I mean: if you have such a wonderful system it would be a shame not to use it to stop copyright infringement in the west, blasphemy (Christian or Atheist literature) in Muslim countries or lack of respect for the dear leader (Winnie Pooh memes) in China.