I'm running all of this on my Mac with vmware fusion so Macosx 10.5 (Leopard) would be the host opperating system. This is an intel machine--vmware fusion only works on intel machines--a mac mini; no monitor if that matters. Debian linux, ubuntu linux, and windows xp professional are all guest operating systems--virtual machines--that run in vmware fusion but I'm not running them all at the same time. I actually own windoweyesadn only use jaws as a demo; both run with software speech and I use the same braillelite as I use with brltty; I'm using a serial-usb cable, usually prolific because debian makes you recompile your kernel yourself if you want to use keyspan. So I usually use the keyspan on windows or in he mac terminal with brltty but I've used the prolific cable in all places too.
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