My first computer was an Apple IIe 128K. I got nine years out of it until it became too outdated to use anymore. Then, I picked up a Mac LC, due to marketing. I was lead to believe that it would run Apple II programs on gear that I already had. That was a lie; I would have had to have purchased very expensive Apple hardware specially structured to use with the LC. I was less than pleased. I got another nine years out of the LC, even so, but I finally gave the Apple IIe and all its software and gear to a synagogue.
I caved in and shifted to a Windows machine after the LC. Too much software that I wanted to use refused to be released in a Mac version, and so I gave up on them.
Years later, I bought an iPod Classic 120Gig. I had no idea how to use it, and I still fumble around with it. It wasn't as intuitive as I'd been led to believe it would be. I wasn't keen on getting it, really, as I don't tend to be the sort of person who walks around with the earbuds in, listening to my own world. However, I do plug it into the car's radio on long trips, and now I have a docking station that doubles as my alarm clock, so I listen now and then to it. I don't view it as a waste of money, but it wasn't as useful as I'd been told it would be.
Of course, if I have an iPod, I had to have iTunes on my computer. I find it fairly irritating, especially recently. I don't care to buy whole albums if there's only one track I want...that's something I left behind in the vinyl days. I've been running into that a lot more lately... Due to the lack of documentation in how to use the software, I had loaded it with a lot of junk, and I've just finished spending months cleaning it all out manually. It runs a bit faster, thank goodness, since I completed that task, but had it had better documentation, and hadn't been "intuitive" in the first place, I wouldn't have had to waste so much time and effort on it.
For the last six months, we've had iPhones. I like the smart technology, and I have been loading music on it, as well as some apps. The fact that it has speakers makes it somewhat more useful than the iPod, for me at least. I've even been reading books on it, most lately some Mark Twain. I admit that I view it as the proof of the vision of SF writers of the 40s and 50s.
So, what's my point, with this rambling? Just reviewing in my mind my own personal Apple journey. There's been ups (personal computing! access to enormous music library!), and downs (forced use of specific hardware! poor documentation of systems!). But Jobs & Co. have had a lot to do with how the tech world works in the world today, and he will be missed.