So I made myself a sort of client-side phone callback system: https://youcallme.io.
It initiates a conference call with you and the customer service line letting you enter the DTMF tones. Then you hang up while it waits for a human to be detected. Have been playing with a few different human detection approaches from call screening to a bit of ML. Once detected calls you back to join the conference.
So far has saved me 45 minutes with Questrade and 2 hours with CRA (Canada's IRS).