OK, as a techie in general, and a pretty rabid Mac user specifically, I often get asked about which is better - Apple or Microsoft. This is of course a pretty loaded question, so I thought I'd separate this into at least two parts - the companies and then Macintosh OS X vs. Windows. Maybe after that I'll do something about the consumer electronic products as well.
So biases up front. I formerly actively worked at Microsoft as a Software Design Engineer in Test writing test tools for a variety of products, most the reader probably never heard of. Microsoft considers me to be a full-time employee on military leave, and I do hold Microsoft stock. I have never had any association with Apple, and do not own Apple stock.
My personal view is that there are many similarities between the two companies, although some significant differences. In particular, both companies tend to be proprietary when it suits them, make SKU choices that are annoying and limiting to customers (although I think Microsoft is worse in this), and have little interest in promoting competition, often through pretty heavy handed methods. Both companies also have highly visible patriarchs, i.e. Bill Gates and Steve Jobs. The companies differ primarily in two ways: Microsoft takes a generalist approach of attempting to create products applicable to anyone and everyone and Apple focuses on a very specific set of products (their own) to ensure a positive and stable experience. The other major difference is in marketing - Microsoft is relatively open, announcing new products early and promoting active feedback from a larger community where Apple primarily maintains a heavy amount of secrecy, surprising both their supporters and competitors with new products. This second difference in particular greatly affects the corporate culture.
Similarities
So first the things the companies have in common. Throughout the history of both companies, there have been existing capable standards that have been changed or ignored to create proprietary systems with no real obvious benefit. A good modern example of this is in digital rights management. MP3 files for audio have good compression, excellent audio quality, and are playable by nearly any music player in existence. The two companies of course have proprietary standards (Windows Media and iTunes), which with DRM enabled (both formats don't require DRM, just support it) limits the options legal customers have for playing their own music by invoking a licensing mechanism.
Microsoft makes serious distinctions between versions of Windows... Why must servers run only on server operating systems? Technological reasons? I'm convinced not really. Apple makes iPods inaccessible as a USB mass storage device. Why? Because then they would lose control of making it accessible in iTunes only.
But that's a business model. Where it gets irksome to me are the occasional heavy handed means both companies use to enforce their proprietary standards. Although I'll give a recent black eye to Apple for its handling of the iPhone 4 leak to Gizmodo, Microsoft's past actions to "encourage" their customers to promote IE over Netscape are little different.
The moral of the story is that both companies are large. Both are for-profit, so both have an interest in promoting their own products over others.
Differences
Probably the biggest single distinction between the two companies is generalist vs. specific focus. In other words, Microsoft produces no PC's but does produce an operating system to run on all PC's. Apple produces PC's and produces an operating system that runs only on those PC's. This necessarily means that Windows works across a plethora of systems, configurations and costs, but Microsoft can guarantee and support little; but that Apple systems are few and cost (much) more, but Apple can guarantee and support much.
I'll talk about this significantly more in the next part, but this focus really is critical in understanding the real cultural differences in the companies. Since Apple produces a small number of different models (the Apple Store currently lists 21 models in 6 different types) they must clearly differentiate themselves from the hundreds if not thousands of competing PC models. Microsoft on the other hand has the daunting challenge of continuously producing operating systems and software that work well on thousands of different kinds of machines, few of which the company can directly test against.
Microsoft, therefore, both internally and externally is a very social company. I remember even as a relatively young child of my father beta testing Windows -- not primarily as a developer, but as a user. Microsoft's frequent beta's and release candidates may be much maligned (even by me) for instability, but shows a strong commitment to letting many people be involved at all levels of development. Internally, I found Microsoft continually preaches about diversity, highly promoting a multi-cultural environment. On the downside, the company so promotes diversity that people (like me) who hold religiously conservative positions may feel very lmited in expressing those positions at the workplace.
Apple may have some of this in common, but as an outsider it doesn't feel like it. Returning to the iPhone 4 leak, I read about Apple's security practices, and needless to say, I can't imagine working there. The idea of constantly being watched by a camera, or not being able to share projects that I'm working on with my friends would drive me nuts. Microsoft wants to show off their nifty products, Apple wants Steve to show off their nifty products.
Conclusion
So how do I feel about the companies? Both companies do things I don't like. I am not a fan of DRM in particular, and I wish that both companies would be more open and less proprietary. But they have different focuses and hence there are signficant differences.
Although I haven't mentioned before now the obvious other alternative, Linux, I have in the past gone through "Microsoft hating days" where I would switch to Linux (I've used Red Hat, Unbuntu, and OpenSUSE). Although I appreciate the truly community focus and open standards, what's always brought me back was consistency and compatibility with a commercial base that only comes from commercial operating systems. And to that I tip my hat off to Apple, who has to date brought out the only consumer-oriented commercially successful Unix-like operating system. Which is an excellent segue to my part 2... Operating systems. Please comment!