Honestly I've been feeling the same way lately, not so much about iTunes but about the post-iPhone, post-Steve Jobs Apple. I've been a Mac user for over 10 years. In 2006 it felt that Apple was fully devoted to the Mac and its Mac customers. It made computers that fit the needs of a wide variety of people, from casual users to power users. Its hardware was upgradeable, even if it sometimes meant needing to unscrew a lot of screws (but this was not true in highly accessible models such as the Power Macs and the MacBook). OS X was absolutely fantastic. It was heads and shoulders better than Windows XP and Windows Vista, and desktop Linux was a major hassle back then, especially for laptop users. Quite frankly, the Macintosh of the mid-2000s was the closest thing to personal computing perfection I've ever experienced.
But once the iPhone came out and became a major success, it started to appear that Apple was neglecting the Mac. Hardware refreshes, which used to occur roughly twice a year for most models back in the mid-2000s, started to reduce in frequency. Thinness and lightness started to become the design goals at the expense of upgradeability and performance, first with the soldered-on memory of the original MacBook Air in 2008 and with the non-user serviceable battery in the 2008 uni-body MacBook Pro. Then once Steve Jobs passed away in 2011, these trends started to intensify. The soldered-on nature of the MacBook Air spread to the MacBook Pro. The easily serviceable white MacBook was discontinued. The Mac Mini, which at one point had user-upgradeable RAM and had an option for a quad-core Intel Core i7 processor, was nerfed, with no quad-core option and with soldered RAM. Even the iMac got the soldered RAM treatment, except for the high-end 27" model. The only truly upgradeable and expandable Mac, the Mac Pro, was transformed from a mini-tower to a modern day version of the G4 Cube, but with no expansion slots (the G4 Cube had one slot, if I recall correctly). And while Apple's hardware offerings increasingly became non-upgradeable and compromised, Apple's refresh frequencies started dragging out dramatically; the worst being the Mac Pro, which hasn't been refreshed in three years, an eternity in the computing world. And I haven't even gotten into the port situation, especially with the new MacBook Pro.
The sad thing is that for me and other fans of Mac OS X, there are no longer any "no compromise" personal computer solutions these days like what Apple used to provide back when the company was fully devoted to the Mac. I assessed the situation in 2013 and ended up holding my nose and buying a MacBook Air despite my dislike for non-upgradeable hardware since I didn't want to have to deal with Windows 8 and the controversy surrounding GNOME 3/KDE 4 at the time. Now it's 2016 and the situation regarding the Mac has worsened. Today's Macs are not much of an upgrade from my 2013 MacBook Air, although I hope my out-of-warranty MacBook Air will last me a few more years. The PC world has a wonderful selection of hardware at every price and performance point imaginable, which appeals to me. Unfortunately, buying a PC means having to deal with Windows or desktop Linux. While they've come a long way since the days of Windows XP and 2005-era distributions, they are still, in my opinion, far behind Mac OS X when it comes to consistency, polish, and productivity. Two weeks or so after Apple announced its 2016 MacBook Pro, I bought a refurbished ThinkPad T430 to familiarize myself with Windows 10. Windows 10 isn't that bad, but I ran into an annoying problem regarding drivers. When I tried to insert a USB 3.0 thumb drive into the USB 3.0 port, Windows complained that it couldn't recognize it. My MacBook Air had no problems recognizing it. I tried updating the drivers on my ThinkPad; still no good. Finally I installed FreeBSD on my ThinkPad. It recognized the thumb drive perfectly fine. If drivers for a common laptop are more of a hassle on Windows 10 than on FreeBSD, something must be wrong.
It saddens me that after decades of Apple providing an alternative commercial platform for those who won't do Windows, Apple has given up, not because Microsoft has crushed it, but because Apple now has a reliable revenue stream coming from its consumer electronics devices and from casual Mac users and no longer needs to cater to more-demanding users. Unfortunately what this means for us power users is that we have been handed over to the world of Windows and desktop Linux, and there is no modern-day polished third party OS like BeOS, OS/2, or OPENSTEP out there for us in 2016. It's really sad, and I don't think there's a viable solution. We power users are a niche market, and nobody is going to invest the millions of dollars and the major engineering effort needed to build an OS (or even a Linux desktop environment + an app ecosystem) that is as polished as OS X just to placate a bunch of disaffected Mac power users.
Sadly it looks like I'm either going to need to hold on to Mac hardware like how many people in Cuba hold on to their 1950's American cars, or I'm going to need to suck it up and learn to love Windows and/or the Linux desktop. I apologize if I sound too melodramatic, but I feel like I've been abandoned with nowhere pleasant to go to.
I've never been an Apple user but I feel you. For me the most baffling part is that a company with supposed hundreds of billions in cash reserves is just sitting on their bottom ignoring a good chunk of their users. I've heard some news that they fired a lot of QA engineers as well but I have no clue if that's true or not.
It does make a lot of sense to keep a strong hold of your market even if you are struggling. Even if you don't have good ideas about innovation, periodical hardware refreshes and opening up a little would project an image of you planning to return, even if it's 2-3 years down the line.
The lack of action from Apple's side however is the most non-sensical reaction in this situation. I honestly can't explain it -- unless we assume that bean-counting businessmen forbid any action where no big profit margins are visible.
As for the current PC/laptop landscape, you might be a little too melodramatic. Windows 10 is an extremely capable consumer-grade OS and while it absolutely doesn't have the polish of macOS, it's the OS that works with the most hardware in history (I was really surprised to read you had a problem with your USB dongle; I have 5 different brands of dongles, USB Type-A and Type-C alike and they worked out of the box) and shows a lot of potential for the near future.
I do agree that the [former] attention to detail Apple showed was unmatched. It's a huge loss to simply let a good chunk of your users go.
More then 90% of that cash is overseas, and Apple is not going to bring it back to the US. (Maybe at some point they'll move engineering where the cash is so they can put more of it to use.)
I had a kind of similar feeling: the Mac hardware tag price is going higher and higher while its performance doesn't come close that of PC, but on the other hand I utterly don't want a PC running Windows 10.
I actually like Windows a lot: I was running Windows 7 as my main operating system on my Macbook Pro for years (until HDD problem, and sadly Windows cannot be installed on a disk connected to the optical sata connector). But I hated the UI nerfing coming with Windows 8. I used it nonetheless because I needed it for Windows Phone development.
But Windows 10 is another whole story. Beside the very unpolished UI, the major blocking point for me is the forced update system. Not that minor updates is a problem, I would apply them anyway, but Microsoft also releases entire new operating system via this system and brand them as updates (eg. Anniversary Update). This can break compatibility, this can mess up the whole system (it happened for each release so far) and it is totally unacceptable for me, as a computer science educated people, to let a third party replace my whole system on my hardware without my consent.
Because I don't except the Mac situation nor the Windows 10 one evolving in a way I like in the foreseeable 2 or 3 years, so I end up buying a Macbook Pro retina 2015 with 256GB and French keyboard layout. Note that I only did that because I'm in a short trip in Japan and the yen/euro conversion rate helped my paying 1214€ for a machine sold 1 689€ at home (= 475€ off) and I wouldn't have buy a new Mac at its full French retail price. I love the retina screen, but I feel forced a bit forced in my buying.
But once the iPhone came out and became a major success, it started to appear that Apple was neglecting the Mac. Hardware refreshes, which used to occur roughly twice a year for most models back in the mid-2000s, started to reduce in frequency. Thinness and lightness started to become the design goals at the expense of upgradeability and performance, first with the soldered-on memory of the original MacBook Air in 2008 and with the non-user serviceable battery in the 2008 uni-body MacBook Pro. Then once Steve Jobs passed away in 2011, these trends started to intensify. The soldered-on nature of the MacBook Air spread to the MacBook Pro. The easily serviceable white MacBook was discontinued. The Mac Mini, which at one point had user-upgradeable RAM and had an option for a quad-core Intel Core i7 processor, was nerfed, with no quad-core option and with soldered RAM. Even the iMac got the soldered RAM treatment, except for the high-end 27" model. The only truly upgradeable and expandable Mac, the Mac Pro, was transformed from a mini-tower to a modern day version of the G4 Cube, but with no expansion slots (the G4 Cube had one slot, if I recall correctly). And while Apple's hardware offerings increasingly became non-upgradeable and compromised, Apple's refresh frequencies started dragging out dramatically; the worst being the Mac Pro, which hasn't been refreshed in three years, an eternity in the computing world. And I haven't even gotten into the port situation, especially with the new MacBook Pro.
The sad thing is that for me and other fans of Mac OS X, there are no longer any "no compromise" personal computer solutions these days like what Apple used to provide back when the company was fully devoted to the Mac. I assessed the situation in 2013 and ended up holding my nose and buying a MacBook Air despite my dislike for non-upgradeable hardware since I didn't want to have to deal with Windows 8 and the controversy surrounding GNOME 3/KDE 4 at the time. Now it's 2016 and the situation regarding the Mac has worsened. Today's Macs are not much of an upgrade from my 2013 MacBook Air, although I hope my out-of-warranty MacBook Air will last me a few more years. The PC world has a wonderful selection of hardware at every price and performance point imaginable, which appeals to me. Unfortunately, buying a PC means having to deal with Windows or desktop Linux. While they've come a long way since the days of Windows XP and 2005-era distributions, they are still, in my opinion, far behind Mac OS X when it comes to consistency, polish, and productivity. Two weeks or so after Apple announced its 2016 MacBook Pro, I bought a refurbished ThinkPad T430 to familiarize myself with Windows 10. Windows 10 isn't that bad, but I ran into an annoying problem regarding drivers. When I tried to insert a USB 3.0 thumb drive into the USB 3.0 port, Windows complained that it couldn't recognize it. My MacBook Air had no problems recognizing it. I tried updating the drivers on my ThinkPad; still no good. Finally I installed FreeBSD on my ThinkPad. It recognized the thumb drive perfectly fine. If drivers for a common laptop are more of a hassle on Windows 10 than on FreeBSD, something must be wrong.
It saddens me that after decades of Apple providing an alternative commercial platform for those who won't do Windows, Apple has given up, not because Microsoft has crushed it, but because Apple now has a reliable revenue stream coming from its consumer electronics devices and from casual Mac users and no longer needs to cater to more-demanding users. Unfortunately what this means for us power users is that we have been handed over to the world of Windows and desktop Linux, and there is no modern-day polished third party OS like BeOS, OS/2, or OPENSTEP out there for us in 2016. It's really sad, and I don't think there's a viable solution. We power users are a niche market, and nobody is going to invest the millions of dollars and the major engineering effort needed to build an OS (or even a Linux desktop environment + an app ecosystem) that is as polished as OS X just to placate a bunch of disaffected Mac power users.
Sadly it looks like I'm either going to need to hold on to Mac hardware like how many people in Cuba hold on to their 1950's American cars, or I'm going to need to suck it up and learn to love Windows and/or the Linux desktop. I apologize if I sound too melodramatic, but I feel like I've been abandoned with nowhere pleasant to go to.