My word choice is more colorful than the source, but I think it's a fair characterization of the message in the source material, and not a proposition I am making myself.
For EFF to issue a sweeping recommendation that users should "avoid Microsoft products where possible" is completely ridiculous and might cause many readers, if they believe EFF to be credible, to conclude that Microsoft is a piece of shit. After all, it would be pretty shitty for a major software company with tens of thousands of employees, many of whom are brilliant, and $2B per month in earnings, to be completely unable to deliver software that does not so imperil users that the general advice is for them to avoid using the products at all. So, given its implications, I think the advice given by EFF is just outrageous.
Saying that IE and Outlook are difficult to secure is not in itself inflammatory, except when coupled with the general recommendation to avoid Microsoft. ANY Internet-connected software is difficult to secure and audit, so why single out Microsoft? Are the other vendors that much better? I doubt it. Can you show me some kind of real data demonstrating that products similar in functionality to the latest versions of IE and Outlook are truly less difficult to secure?
The argument that "adversaries tend to attack popular platforms" is common sense but not useful, and no more compelling than saying "The vendor with the largest installed base, the most smart developers, and the most cash, will do the best job, over time, of securing their platform." In reality, the size of the user base, and the size of the company, provide nothing more than a rationale, as opposed to real information about the security of the platform.
So, in my opinion, EFF is not making a "fair assessment."
This is not you and me having a debate over beers at a bar. This is the EFF saying, flat out, MS products are to be avoided, and one reason for that is their popularity. For most people, this translates to, "Use a Mac instead. They are inherently more secure and less of a target because they aren't as popular." And while there are lots of great reasons to use a Mac, I think this line of thinking is flimsy.
Finally, the MS bashing fest is totally pervasive. It's firmly in the zeitgeist right now, and I totally object to the herd mentality it demonstrates. Last week there was a much-debated post on HN by a company indicating that an experienced .NET programmer is "ruined" and very unlikely to be a good programmer in general.
There are absolutely valid criticisms of Microsoft. But when every jackass, and "credible" sources, too, develop the reflex that Microsoft is shit, it offends my sensibilities.