Picto makes the game less fun

[GoatOfWar]

But I don't necessarily think that more challenging jobs should have better damage output than easier jobs.

That's a good way to make people abandon more challenging jobs which will then inevitably result in simplification, as we've seen before. If there's no reward for your efforts, why bother?
If you seriously think people just arbitrarily want to work harder for less reward, or equal at a maximum, i think you might want to talk to some people who actually play those jobs.
It's such a bizarre idealistic take, usually held by people playing the jobs that conveniently are notoriously easy.
What you'll inevitably end up with in practice is everyone flocking to the training wheels job instead. As people don't want to be penalised.