First of all, I'm fairly heavily anti-apple and have been since pretty much forever so maybe take that into account when weighting the following - having said that, I'm very "techy" to use a generic phrase so generally know what I'm talking about.
Apple has a long history of trying to (forcing) owners of it's products to allow Apple to continue to control how you use products after purchase. They use a huge number of completely proprietory parts so repairs are difficult/expensive and usually also proprietory connectors (which they'll happily licence for huge sums). Not so sure about recently but in the past Apple have frankly not given a crap about it's products being in any way compatible with anything they don't sell or get a licence fee from, so USB support has always been pants. If you buy a USB MP3 player from pretty much ANYONE else, you'll usually see a huge improvement in compatibility with in car systems, desktop, laptop, Linux, Windows, even Apple products because they don't try to overcomplicate things.
They then spend a fortune on marketing so people think it's the best, must have but in reality, Research and Development makes up less than 2% of it's costs - which is frankly ridiculous for a technology company. On average tech companies put just under 10% into R&D.
If you're heavily invested in the Apple ecosystem (ipod, iphone, imac, ibook ipad etc) then, and only then, is any of the stuff they produce really worth considering - otherwise, you can pretty much guarantee that you can get much better gear for the money, or save a good chunk for equivalent stuff.