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The USB player I had at the time that the iPod came out was way easier to use. The player I had you could plug into any computer and simply copy a file.
Which is fine if you want to listen to one song. But most people prefer to listen to multiple songs.
So you've been using your media player for a while, full of music, and you decide you want to change what you're listening to. You can't just sync in a new playlist like you can on the iPod -- you wind up having to manually delete the songs you don't want in there, make sure the directory structure is correct, and then move in all of the songs you want to add.
And hope that you only ever want to organize or select songs based on album, or perhaps artist. You don't easily have the option of selecting songs off your hard drive by genre, or perhaps by decade, unless you've pre-organized your music in this manner (in which case, adding songs by album or artist is probably going to be impossible, unless you've manually maintained some huge directory full of symbolic links to organize your music along multiple vectors simultaneously). Again, doing this is ridiculously simple on the iPod, but it's a chore on media players that just present themselves as a mass-storage device. You wind up doing all the things that a computer is good at handling by hand.
And that's fine if you like that. Some people like chores. I know some people who love sweeping their floors. I'll stick to my Roomba. There are tasks that machines are simply better at than humans are, and if you like to do those things yourself, more power to you. I'm not trying to put down your choice of device, but don't fool yourself into thinking that it's easier than plug-and-play synchronization (and if you had to "go through all kinds of options to sync" an iPod, you were doing it wrong).
Again, this is one big reason why the masses flocked to the iPod. For most people, dragging music around in a UI to load up their device is boring busywork that wastes their time. The iPod only ever asked them to plug it in, wait, and go.
The trouble for Apple today is none of this new stuff they are doing (iWatch, iTV etc) has anything near the wow factor anymore.
I can agree with that, although in a somewhat qualified manner. Apple has always been pretty open that the Apple TV is more of a hobby device for them. It shows, especially outside the US where the app/"channel" support is pretty pathetic. Here in Canada, it's really only useful for Netflix and iTunes content (I bought one for my parents a few years ago after the last video rental shop in their town closed; my father, who is virtually computer-illiterate, loves it for renting movies). I own a lot of Apple gear (although not exclusively), but have avoided the Apple TV as other that Airplay, I can't figure out what I'd use it for (we already have three devices in our entertaining centre that can play Netflix).
But you're right -- neither have much of an immediate "wow" factor. The only devices they seem to be somewhat hitting with "wow" is with their new laptops -- I do find it pretty hard not to be impressed by the latest MacBook, and look forward to getting my hands on one in a store to check it out. That, however, is a different market than their consumer electronics like the iPhone, and isn't going to drive the same sort of uptake as the iPod and iPhone did.
In Canada, the only notable services we have are the iTunes Store (of course), Netflix, Crackle (if you like watching the same ads over and over even in the same breaks), Crunchyroll (if you like anime). There's also YouTube and Vimeo.
I think you might be selling Shomi and Cineplex Online a bit short. Both seem to be fine services -- what is really holding them back is a near total lack of device support, making it more difficult to integrate them into the living room (or in the case of Shomi,needing to be a Shaw or Rogers customer).
I recently cancelled my 90 day free Shomi trial. It's more geared towards TV binge watching it seems -- while it has movies, its selection is sparse, and in some cases duplicates what Netflix already provides. I'm not much into TV shows, however my wife may have watched it if it had actually been available on any of our smart entertainment devices. They technically support cable boxes from Shaw and Rogers, but that doesn't include much in the way of browsing; you have to use another device to find what you want to watch, flag it, and then find it on your cable box's "On Demand" section as a saved item. Perhaps even more stupid, the service just started three months ago, and the only other non-PC and non-phone/tablet device they support is the Xbox 360. Way to aim for last generation there, guys!
I've never even used Cineplex's offering, even though it looks like a pretty decent service overall. Again -- the device support just isn't there for set-top devices, although it seems to be better than Shomi. They also support the Xbox 360, the Roku 3, and some LG and Samsung smart TVs.
Then there is the National Film Board of Canada (NFB). Nearly their entire collection is available to watch online (http://www.nfb.ca) -- over 2500 films. I was surprised to learn that they do have some device support (Roku, LG Smart TV, Samsung Smart TV, Panasonic, Google TV, Opera TV, Philips). No Playstation (or Sony TV/BluRay player) or Apple TV support, unfortunately.
The CBC would seem to be ripe for this sort of streaming service. Their iOS app already has a full compliment of all of their shows and original programming available to watch free on-demand, as does their website. They also have streams of all of their radio stations, again for free. I'm rather surprised that nobody has done the footwork to get their content on their devices (beyond PCs and iOS/Android mobile devices).
So I'd argue that the content is there -- it's the device support that sucks. It's all over the place. You might get two or three services with a Roku, but for others you'd need an Xbox 360. Apple Canada should be pursuing more of these sorts of connections. It's bad enough we don't get many of the US service like Hulu here, but it feels nearly criminal that we also don't even get was access to the existing Canadian services either. The services are there -- it's the lack of widespread device support that is hurting them.
On the other hand, maybe that's a bad idea, as I may then have to sleep forever...
This is why, even though I do own a bunch of other Apple gear, I don't own an Apple TV. The Apple TV "channel" selection here in Canada is pretty pathetic. And while we do have a variety of online streaming services at our disposal (Netflix, Shomi, Cineplex Store, NFB, and probably a few more), none of them are available on the Apple TV, other than Netflix (indeed, many of them aren't available on ANY devices outside PCs (Windows/OS X, and sometimes Linux), or phones/tables (running iOS or Android)).
Honestly, the only thing the Apple TV potentially has going for it is Airplay support, which would allow me to use my iPad to stream stuff to the Apple TV, or to use as a secondary wireless display for my MacBook Pro. It's cheap enough I might buy one someday just for AirPlay, but otherwise the online services are sufficiently pathetic outside the US that it makes it hard to really get excited about.
Apple needs to spend more time in international markets like Canada in getting more content. Or they should just open up the device to 3rd party developers ala iOS, and permit "channel apps". All of the big networks in Canada already have iOS apps for streaming and watching shows online; porting these to the Apple TV should be trivial, and would open up a huge world of possibilities. I already have the HDMI interface cable for my iPad so my wife and I can watch content we may have missed, and so my wife can watch TV from her home country -- being able to do something like this directly on the Apple TV would be greatly welcomed (that, or have more such apps available on the PS4, which is already part of our entertaining system).
MP3 players arose in a time when PCs in general were still primitive. They suffered because of this.
Which only reenforces my point that Apple came along, and won the market by introducing a device that didn't suffer from these issues. And a huge part of that was the end-to-end software integration that all the other device manufacturers ignored.
At that time, CD ripping was already simple. Buying ready made content was only a problem because of a sandbagging cartel.
Sure, you could pop open some piece of software and tell it to rip tracks from your CD player, resulting in a whole bunch of files name TRACK_XXX.MP3, but then you had to manually do the work of naming them, organizing them into an album, and getting them into your MP3 player (as your mp3 player-of-choice's sync software of the day typically didn't include its own CD ripping software). It was a chore. iTunes did away with all of this; it had a built-in CD ripper, it used CDDB (now Gracenote) to automatically tag track data, it uses a database to automatically categorize and organize music along multiple vectors.
Sure, the parts were there for other MP3 players, but getting them all integrated together was a chore, and not one likely to be undertaken by your average everyman. The iPod integrated all of these things together, making ripping your CD and putting it onto your iPod as easy as insert CD, press button, plug-in iPod, wait. It took the chore out of it, along with the need to get together all of the disparate pieces of software you'd need to do the task, as it was with other MP3 players. That is why the iPod won.