My Pet Theory...
To argue that IS/IT guys want an easier to manage computer entirely misses the reality of human nature. First, and foremost, what IS/IT guys want is to be needed. Computers and the IT department are their fiefdom. When something goes wrong, they get to swoop in as the Knight in shining armor to fix the problem, and save the damsel in distress. Threaten to make the overall experience easier, and you threaten the very existence of the IT/IS guy. He will not stand for this.
In the early days, the IT/IS guys were composed of your basic computer geeks. They loved command line operations. It was a language that only they understood, and this gave them importance and purpose. With an Apple on her desk, the IT/IS guy wasn't needed.
So, when the computer buying decisions were being made, they were being made by these very same IT/IS guys. And their choice was natural. Apple never had a chance at this.
Skip ahead 20 years. The market is what it is. Apple is a niche computer company. So what? They are a healthy business who turns out great products. I buy their products because they work for me. I like pluralism. I like living in a society where there are choices. Marketshare is proving not to be as important as everyone makes it out to be. Sure, Apple can grow their own customer base, and this will be a good thing. But, there is no chance that they will take the market away from MS in any significant numbers in the next 20 years. So what. They can and will be a successful company regardless.
And, speaking of price. The last thing I want Apple to do is to cheapen the components and design of their hardware so that they can sell a box as cheaply as Dell or the other computer companies. These companies routinely use sub-standard materials so as to get to a certain price point. We saw a move in this direction under Gil Amelio, and I think it was disastrous for Apple. Just as Mercedes Benz should never beat out Hundai on price, Apple should never compete on price alone. I'll pay more for the better machine, thank you.