As a firm Linux user, who has got no windows influence in my household, entire family gone Linux in some shape or form, I can't see as a power user how he is prepared to make this switch.
I know that Linux so often makes you put up with compromises and so often it is at the graphics card hurdle that it starts to annoy, but I think the 3 things he'll miss is the things which will eventually drive him back.
Firstly, the shell is one thing that seems irreplaceable, yes you could use cygwin or equivalent but nothing will fill the void of a shell that is so beautifully incorporated into the OS, more than OSX in my mind, despite them being the same shell, Linux makes no excuses and is proud of its Shell.
Transparency, Yes this is important, but something I know I could live without, as he mentions he doesnt do this as often as before and really its main purpose was for fixes with drivers.
Package Management and I would stretch further to even open source and free software will drive him back. I had a stint where I could only use Vista for about 7 days, the reminder of the horrors of "shareware" software and 30 day trials had me looking forward to getting back to "apt-get install"
I agree that a switch to Windows does not make sense. I fled to OS X because I'm a Unix biggot and don't want a system that doesn't ship with zsh or bash. Apparently darwin's posix API sucks and is different from Linux but I'm not affected by that directly so don't really care.
Cinch, SizeUp, and Divvy provide all the tiling things I need for window management and they unobtrusively just enhance my normal environment, it's great. I don't miss xmonad at all anymore. I miss dpkg and apt but homebrew is good enough and I regularly fire up Linux VMs if I just need to, vagrant is awesome for this. (vagrantup.com)
I know that Linux so often makes you put up with compromises and so often it is at the graphics card hurdle that it starts to annoy, but I think the 3 things he'll miss is the things which will eventually drive him back.
Firstly, the shell is one thing that seems irreplaceable, yes you could use cygwin or equivalent but nothing will fill the void of a shell that is so beautifully incorporated into the OS, more than OSX in my mind, despite them being the same shell, Linux makes no excuses and is proud of its Shell.
Transparency, Yes this is important, but something I know I could live without, as he mentions he doesnt do this as often as before and really its main purpose was for fixes with drivers.
Package Management and I would stretch further to even open source and free software will drive him back. I had a stint where I could only use Vista for about 7 days, the reminder of the horrors of "shareware" software and 30 day trials had me looking forward to getting back to "apt-get install"