If I’m using the CLI directly in a Linux vm I use tdsr. If I’m trying to use JAWS or NVDA to read the output I’ll ssh into the vm using PuTTy.

Emacspeak is great if you can get it working. It's very difficult to install, especially on Mac OS, and the learning curve of Emacs itself is high. But it's an amazing tool if you can get there.

I've had mixed success with Orca. It's maintained, though in terms of functionality it's a little disappointing. It only works in some desktop environments, and of course the website doesn't tell you what those are. I don't use it but I know people who do some some success.

Probably the most reliable (but in its own way limited) approach is to use a distro like Talking Arc with Speakup, which reads the command line. THis won't help with graphical stuff but it's fine if you don't want or need the graphical UI.

http://www.linux-speakup.org/

A project to follow (with an active mailing list) is Raspberry VI, dedicated to getting screen readers to work on the Raspberry Pie. They've come along way, as has the Pi.

http://www.raspberryvi.org/stories/index.html

I use tdsr for the terminal and emacspeak for coding on a Mac, both were far easier to set up then I expected
If you're using a raspberry pie then apt-get install emacspeak should work fine, might have to get a tts server too though I didn't for some reason and it worked
You can plug in headphones or a speaker to the pie and it will work perfectly

I would like to add if you have a Braille Display, BRLTTY is amazing.

I'll enthusiastically second both Emacspeak and Speakup. ON the contrary, I found EMacspeak on Mac OS to be quite easy to install, but this isn't really a topic about that in any case.

Speakup is part of the kernel in most modern distributions, though it mighht be a bit hard to get going. DO you have a soundcard for the PI? YOu'll need one, Espeak, and a program called Espeakup, which should be available via apt or whatever tool you use.

I ran Linux for about 8 years, but I returned to Windows around last Christmas. I finally realized I had to be practical. It does not matter if your computer respects your freedom, when you can't get access to the programs you need. I would like to return to Linux someday, but programs like Orca have some catching up to do.