As a great proponent of software freedom, digital (and other) privacy etc... I can applaud the FSF for bringing to light the issues with common software and hardware and offering alternatives. However, from a practical standpoint, as others have said - these items are only alluring to those who value software freedom above all else. Why? These items typically will be less functional, easy to use, or are otherwise encumbered for all but those who see the value of software freedom and are willing to put in the effort to use it despite the above.
While I know the FSF needs to have uncompromising ideals and push for them - , I do think this can be a starting point for the Linux, FOSS, privacy/security etc... community to use as a learning experience for how to mate the ideals we value to the pragmatic needs of others, especially non-gurus. Taking the items provided as a basis, perhaps we can go a little further..
OS: The FSF suggests Trisquel and an alternative for Windows. While the idea of submitting a Linux distro as a substitute OS is a good one, the difference in experience between Trisquel and Windows for a Windows user may be staggering. This is a distro that does not include, even as an option, anything with a license that doesn't meet FSF standards of freedom. Thus, you're losing a lot of things there even compared to other Linux distros. Telling someone "Oh hey, try this new OS out on your laptop, it respects your freedom and privacy. But uh... your wireless card may not be supported. Sorry. Here's a list of additional dongles you can buy that are supported, through!" isn't going to go very far. There are many distros that may be a better compromise out there. Linux Mint Debian Edition for instance (or even plain Debian) protects a user's freedom/privacy (something Ubuntu sadly, does not), but gives many more options including things like the use of 3D binary GPU drivers etc.
3D Printer - While I'm not versed in depth regarding the state of 3D printing comparisons, it seems like the Lulzbot is a great alternative to the Makerbot; competitive in cost and functionality, while being Free hardware and software. However, it does not seem to be currently available, instead being on backorder. Hard to consider a holiday gift item that may not make it by the holidays! The bigger issue with this item instead is that a 3D printer is a very niche device, especially one as expensive as this. There could probably be a lot of other options for this entry instead; I'll go into that later.
Gift Cards - This was just a missed opportunity. While I do think that a FSF donation/membership gift could be mentioned, this is again a very niche community that is best sought out by those who are most interested. Those without the technical interest and know how, will probably think "gee...thanks" and look at it the same way as if someone bought them one of those "congratulations, someone has purchased a cow for some impoverished people somewhere in your name!" - unless the person is very into the "cause", its not so much a gift for them as it is spending money on something the buyer values but the recipient may not. However, there are tons of alternatives for an iTunes giftcard that would be a good FOSS analog. How about one of the DRM-free media stores, like Magnatune or 7Digital? Even FSF's own Defective By Design campaign lists many of them - http://www.defectivebydesign.org/guide/audio - wouldn't this be a better alternative, showing people that they can buy music unencumbered by DRM elsewhere?
Laptop - This is where I get a little frustrated. I'd love to go out of my way to buy a Libre laptop, or even just one that comes with Linux installed and supported natively. However, so many of the Linux system integrators..well, just don't cut it. Consider that we're increasingly pushing towards "tablet convertible" laptops, ultrabooks, and even luxe power/aesthetic balanced models. 10 point multitouch screens, glass trackpads, high resolution and color gamut displays, new GPUs from both AMD and Nvidia a well as Intel in certain models, backlit keyboards, premium metal chassis and construction, magnetic power adapters and wireless charging. . By comparison, the hardware offered by ThinkPenguin and many other Linux system integrators seem positively antiquated and cheap-feeling. (Admittedly, System76 does seem to take a step above and offers some models with backlit keyboards, a full GPU etc). Big black hunks of thick plastic, typically Clevo rebrands, lacking many features from the aesthetic to the performance related isn't going to show the greatness of Linux. I know I'm a minority who searches for "luxe" laptops that offer high quality features, aesthetics and the best performance/form factor ratios available and have been saying for years, I'd love to buy a laptop that had pretty much all the features and more, plus the aesthetic level of the MacBook Pro (or the Razer Blade Pro) but built with Linux and FOSS compatibility in mind. However, even Joe User isn't going to want a heavy, blocky, plastic laptop that lacks the neat features they could find elsewhere. This, moreso than any other entry in the guide is something I think the Linux and FOSS community should consider planning an endeavor to design and have high quality laptops with Linux in mind available for sale.
Ebook - Another missed opportunity. While Project Gutenberg is a great resource for those wanting copies of public domain works as DRM free Ebooks, Joe and Jane user who is thinking of picking up a Kindle, Nook, or another Android tablet isn't likely to be interested in classics. You're not going to be able to get Harry Potter on Project Gutenberg! There are two great recommendations for this category. First, the FOSS software "Calibre", a perfect example of FOSS that is the best in its class. Calibre can manage pretty much any hardware or software Ebook reader application, act as a great virtual library, and convert ebooks between just about any common file types. With the correct plug ins, it can even strip existing DRM (which of course have to be installed separately for legal reasons). It also has a ton of built-in links to ebook stores, many of which are DRM free. Why not suggest some of these? Baen Books for instance offers inexpensive, DRM free ebooks for hardcore science fiction fans. Again, the DefectiveByDesign campaign has as list of its own - http://www.defectivebydesign.org/guide/ebooks . Project Gutenberg is great for what it is, but it isn't going to hook users who are otherwise thinking of purchasing bestselling Kindle ebooks from Amazon.
MobileOS: While I certainly would suggest that Android is superior iOS in terms of freedom, focusing exclusively on Replicant is very limiting. Replicant only works on a few, mostly older, Android hardware. It would be better to focus on Android, which can be configured to use as much AOSP data as possible, and ROM customizations like CyanogenMod, Paranoid Android, and PACMan, that give the user the option to reject Google applications if they wish. How about suggesting the use of F-Droid as an alternate repository, and why it is beneficial? How about talking about The Guardian Project and its applications for protecting privacy on Android? Giving them other alternatives and allowing them to choose (and yes, some of them will choose Google Play and Angry Birds) will encourage them to see the benefits of Android FOSS that apply to them (Hey, this Open Street Map app is really cool. I like it more than Google Maps) without limiting their choices of the games and apps they may wish.
OnlineStorage: Tahoe-LAFS is by far an enthusiast-only solution. Go ahead, check out LeastAuthority and look at the setup steps and then tell me that the average Dropbox or Google Drive user is going to be interested or capable of using it? This just isn't being realistic. Why not look to something a bit more realistic yet still FOSS, like Kolab and OwnCloud, which are user friendly and have options to purchase a pre-configured hosted instance through a variety of vendors like MyKolab and OwnCube, many of which contribute money, time, and code to the projects!
Media Hosting: This isn't actually a bad idea, but a little expansion would be better. Right now, a user can go to YouTube and immediately upload a video and have a link to post on Facebook or give to their friends and family. MediaGoblin isn't quite that easy; when they have complete federation up so that users can seamlessly run their own instances or rent a configured instance hosted for them, that will be a nice alternative. Right now however, it still requires users to have the skill to deploy MediaGoblin on a web-facing server of their own, or find one of the few websites that already offer it. I'd expand to MediaCrush as well, which is ready to use immediately with a public-hosted instance as opposed to just a run-your-own deployment.
In summation, the FOSS community, if not necessarily the FSF, needs to realize the needs and wants of users cannot all be handwaved away just by answering "Well no, you can't...BUT FREEDOM". Yes, software freedom, privacy etc.. is important and we'd live in a better world if these elements were the norm. However, it has to be up to an individual user how much compromise they're willing to put up with to attain these ideals and, perhaps pessimistically, the average response will be "not much". Thus, if we want to make any headway at all besides tiny niches, we need to offer the things people actually want and provide them in an ethical manner. Firefox is a great example of FOSS for instance - Free and Open Source, made for the user not for advertisers or other 3rd parties, extensible and customizable, has tons of great features, and can be used with relative ease by both novices and gurus to do what they wish. It would not have made it to such prominence if all the average and novice users weren't able to find it preferable to other options; the fact that it is FOSS acts as a bonus. These kind of successes each advance the cause of FOSS an openness in general, as users vote with their dollars and clicks. This is what will bring about a future for FOSS beyond just niche tools for niche developers and gurus, realizing that the pragmatism of average users needs to be taken into account!