I thought I would update anybody in case they also run into this issue. After contacting Apple support and visiting my local Genius Bar in Sydney, I was given a new MacBook Pro because my original laptop would not boot off an external drive for further diagnostics. When I upgraded to Mohave after taking the new MacBook back to my office, the same problem immediately returned (on what was a fresh install)!
I have continued to work with Apple support, and also contacted the US based Accessibility and Assistive Technology Support group – they have all been excellent and patient, and we are still trying to isolate the exact nature of my problem. After lots of experimenting with the trackpad and accessibility settings, I have found the problem. I am just waiting to hear back from Apple support to see if this is a bug or a new implementation on how "dragging with drag lock" is supposed to work.
Because I am a quadriplegic, my fingers are curled up and I actually tap the trackpad with the knuckle of my middle finger. It is quite a delicate tap, but it still registers when I have “tap to click” enabled quite consistently. When I go into the accessibility settings and turn “dragging with drag lock” on, the sensitivity of taps for “tap to click” dramatically decreases so that even regular tapping doesn’t work for me – I need to actually click the trackpad to get it to register. If I just tap the trackpad, I am lucky if 1 in 10 taps are recognised as clicks.
I believe it is the above software change/bug in Mohave that has impacted my ability to use “dragging with drag lock”. Because "dragging with drag lock" begins with a double tap, requiring the user to hold down after the second tap, the odds of me successfully "dragging with drag lock" dramatically diminish. That is why I thought the feature was broken. I asked a work colleague to test my trackpad with "dragging with drag lock" enabled and it immediately worked for them.
When I leave "dragging with drag lock" off, "tap to click" works very reliably for me. The moment I enable "dragging with drag lock", I cannot use the dragging functionality and "tap to click" no longer works reliably either. When I change the dragging functionality to “3 finger drag”, I can now drag windows (though with less efficiency than my preferred method) and "tap to click" works reliably. I have also noticed that turning on dragging by "3 finger drag" does not automatically enable "tap to click", so these 2 functions are not linked in the way "dragging with drag lock” is linked to “tap to click”. If “tap to click” is disabled, enabling "dragging with drag lock” will immediately also enable “tap to click” since this is an element of the functionality required for “dragging with drag lock”.
Given that dragging is a software feature, it appears to be either a bug in Mohave or an intended change in the functionality of “dragging with drag lock” in order to reduce accidental dragging. My hunch is that I have uncovered a bug, because “tap to click” becomes almost unusable for me only when “dragging with drag lock” is enabled (but otherwise works perfectly).