Not to defend Apple, but the flip side is trying to figure out which of Dell's 30 or so monitors are current (and which have which connectors). Apple has one monitor (a bit obsolete and a bit overpriced), but you can quickly decide for or against it.
Too many choices may be stressing, but I think you lose out with too few choices too. If you need a specific size monitor to fit a space and the one monitor Apple has does not fit that space, you are SOL.
As other commenters have noted, this benefits Apple more than the average consumer. They can offer one or a couple of options, overprice them, and make a lot of money. Ideally, on such a big purchase (although for mobile devices a lot of the cost is not immediately apparent because you pay comparatively little upfront), someone would seek to reduce their choices by doing research on the various options available and deciding which would work best for them. For the monitor example, first filter by screen size, then filter by resolution, then connectors available, etc. for all the features that are important in that case. The options that are left are the best options available in the judgement of the person making the purchase, and then the decision between a handful of options becomes much easier. They can save money by getting only what they want.
Quickly deciding for or against just the one option benefits Apple the most. You end up trading money for ease of choice. I for one would rather keep my money in exchange for extra research, but it seems today's culture has an extreme phobia of stress (which is a whole other dicussion in itself).
Sorry to pick out one tiny point from your post, but, I truly don't think that much of anything they sell is "overpriced". It's more expensive than competitors stuff, but their stuff...sucks.
When I think about the quality of a shitty Dell, HP, ASUS (enter your choice of brand here) laptop computer that can be bought at 1/2 the price of an Apple product, and how it will probably have a totally dead battery in a year. And that half the keys on the keyboard won't work. And the hinges for the monitor will be close to severing. And that I will have had to hack together a *NIX environment that sort of functions 50% of the time. And that the trackpad will suck. And it goes on.
I will gladly pay for Apple doing the work for me, giving me a machine that will last for literally years without fail, getting me a solid dev environment from day 1 with little to none of my time and effort spent.
Apple has only one monitor, and it is clearly out of date (not ultra resolution, not of same body type as current Apple products). So I quickly figure out I don't want it with no stress.
I am more likely to buy a Dell monitor. But I would be even more likely if the website was more oriented to the task of telling me which monitors are current in each class.
