I must agree with you on some points, such as the excellent resale value I get from iPhones and MacBook Pros, and especially with the MBP the fact that I can keep one for more than 5 years without finding it has slowed to a crawl. A 5 year old Windows laptop is good for only one place usually...
When you look at the pro world of video production and editing and photo editing, Windows doesn't get a look in as the OS just isn't up to it.
Overall cost I would maybe debate, because to get the same level of performance in a Windows laptop, you need to spend a lot of extra cash on memory and SSDs and even then, you probably wouldn't have the same level of screen.
I read Stuff magazine and, although they can't be experts in everything, the MacBook Pro has been the best laptop overall for many years now. No Windows laptop even comes close.
As for proprietary, you could also view that as being ahead of the curve in many ways, for example the MacBook with a single USB-C connector. Everyone moaned like mad but now it makes perfect sense with the rise and rise of cloud storage and web apps.
The removal of the 3.5mm connector. Again so many complaints but now just look at the other manufacturers removing them as well
I definitely value the 'It just works' thing and most of that is due to the fact that the iPhone isn't customisable...one manufacturer, one operating system that almost 80% of owners are using and apps that are only available in the App Store, approved by Apple.
You're right with one thing though...the overall reliability has dropped slightly in the post-Jobs years but is still pretty good I think.
'Old' and 'stale' I'd have to disagree with though. Their laptop screens are always ahead of everybody else's and the MBP body style is now copied by so many others it's a bit of a joke.
When their SSD machines came out they were faster than any other make and that does explain the cost of those machines, trackpads and multi-touch gestures are way ahead of the game as well, but now being copied by others.
Apple are very 'cutting edge' and you can see this now in the other manufacturers copying them.
When Apple brought out the curved edge iPhone 6, suddenly everyone copied it, even down to the speaker grills. Some lead, others copy.
Obviously I really get on with Apple gear, although initially I swore I'd never buy an iPhone. It's just that when I did, it just worked, as they say.
Luckily, there's room for everyone but I was just curious as I've seen the comment 'I'll never buy an Apple product' on here a few times so I wondered why not in your case.
I do understand Audeze's decision to not invest in the many combinations of hardware and Android OS versions out there though and I'm just lucky that I like iPhones and Audeze have catered for people like me.
With the Lightning connector, I can buy an adaptor and then use a USB DAC like the Dragonflies or USB card reader or VGA or HDMI output if I feel like, it so I don't see that as an issue.
I realise it may be disappointing for Android users though but I would really recommend picking up a second-hand iPod and using the Cipher cable. It really is remarkable.
I realise this discussion could go on for days and I didn't intend to write nearly as much as I did, but hopefully it's obvious that, exactly as you say, we all value different things and make different choices...it's a very interesting time to be alive at the moment