They need to find another way, because this isn't going to win over anyone, and it may lead some to believe that free software folk are desperate nutcases (which couldn't be further from the truth). There is just no thought or substance to this campaign at all.
BTW, I wonder why ChromeOS isn't on their list given that ChromeBooks will probably be a popular purchase during the holiday season. And I actually think in terms of arguing for or against an OS, ChromeOS is probably the easiest to argue persuasively against.
For example, you can tell people you can't print to your desktop printer without an internet connection and that every time you print (even to your desktop printer), Google records that action. Some people won't care, but others might not be happy with that. If you then go on to say that Google potentially [1] tracks and records your every action in the OS, you'll be raising awareness of important privacy issues.
[1] I say potentially because Google doen't reveal what they track and record in ChromeOS and that in itself is a question people should ask themselves when they use ChromeOS i.e. is it important for me to know what Google records of my online behaviour? Until Google reveal what they track and record, should I refrain from using their OS?
Also, these other ideas are all based on some compromise: "Sure, go ahead and spend 2 grand on a macbook pro for you kids going to college, but at least leave the breadcrumbs for us poor folk". As much as it can help, it brings no actual progress to the ideals of the FSF. It would be more of a feel-good campaign than anything else.
If you want to promote Free Software, you need to have good alternatives to proprietary systems, but at the same time you need to fight against the mindshare that the giants have.
Why not stand outside an Apple store and hand out DVDs under the motto 'here, free software for your new Mac'? Put LibreOffice, VirtualBox, Adium, and whatnot on it. Insert a flyer explaining what 'free software' means and suggest that they can donate to these projects if they like the software.
Sure, they will be running one OS X. But one step at a time is better than 99% thinking there were approached by nerd Hare Krishnas (nothing against Hinduism, it's about perception).
The thing is: the FSF is supposed to be "nerd Hare Krishnas". They don't - rather, they shouldn't - want to compromise. They are advocating Free Software. Not open source. Not consumer-friendly gadgets. Not "cool things that Apple can't do". They will preach that using anything Apple is wrong, and they are rightfully voicing their views.
Admittedly, not on a disk, but a nice flyer or something for this would be good.
I use it as a canonical example of unusable software.
The reason that people go into the Apple Store rather than buying a fully free software system is that a MacBook Pro Retina is in an entirely different class than a Lemote Yeeloong (one of the few computers that is able to run free software end to end such that Richard Stallman is willing to run it).
I think that working to provide effective free software alternatives, and partnering with hardware companies that supports that mission, would be far more effective than dressing up in a GNU suit outside the Apple store.
People want to feel good about their purchase decisions so you already have a strong headwind you are working against. The problem is that people have specific things they want to do with those new iPhones and iPads. The FSF position is that you shouldn't buy one. There isn't really a middle ground here. If my situation is that my teenager yearns to play candy crush on a new iPod touch for Christmas, the FSF message is completely at odds with that and nothing you tell me outside the Apple store on a freezing cold day in Boston is going to move the needle.