The problem generally comes down to the fact that no Republican is for improving tax filing. So all it takes is for a handful of Democrats to be lobbied to oppose it and even a Democratic majority can't push changes through.
Paul Ryan also proposed something similar. However, Democrats opposed it. Basically if it’s simpler and cheaper taxes, Democrats cry foul. Auto filled forms with the current tax system is just lipstick on a pig.
No, better filing with the same tax system is empirically a better position. Holding auto-filling hostage to push contentious unrelated systemic changes is dirty, and why we have such gridlock. "I'm willing to allow a wide-consensus change but only if you concede me my very contention change" is not good-faith.