What I would do is to find a text that you know well: a favourite book or something like that. If it's something you've memorized, that'd be good as well. Start with that text at slow speed and pay attention to how the words sound. You're not looking for content, but how the synthesizer pronounces words that you know. Then speed the text up gradually until you can no longer understand what it's saying. Then slow it back down but this time not as slow as you'd started with. Just gradually inch the speech up a few words per minute at a time, over a period of a few days, or when you find the current rate is too slow. This is what I do when I encounter a new synthesizer. I find it works rather well. It's similar to learning music. The screen reader keystrokes just take a bit of getting used to, but it will help you if you are a good typist as well. I'd just spend a bit of time every day practicing the keystrokes from your screen reader. If you look for tutorials for tasks you need to do frequently, that's often a good place to start. You might also want to try different voices, as often the default one doesn't work for everyone. I'd recommend finding a voice that sounds pleasant, and that will make it easier to learn. Hopefully you won't end up in the situation that I find myself in where I'm not a big fan of synthetic speech in general. If braille input was more reliable, I'd use that exclusively but I havnen't found a good place to put the braille display near the keyboard because I can't do the old trick of putting the display on top of the keyboard, because it has the perkins-style braille keyboard. I can type just as fast as I can braille, I just find it easier to type because contracted braille input seems to be still a bit buggy with NVDA. I'd try JAWS, but I'm not so sure that the $1500 CAD price tag would get me something that NVDA isn't currently doing. I'd be interested to hear what you're using, though, to help.