Whilst I would agree with many of the things you say, I an not in total agreement. Like you we (my girlfriend and I) are long time users of multiple Apple products, currently; Apple TV x 2, MacBook, iMac, iPad Pro 9.7, iPad Mini 2 and two iPhones (6S and 6 Plus).
I have been using my iPhone 6 Plus for nearly two years now and am planning to purchase a new phone soon. I always buy unlocked. I have been casting an envious eye at the new Samsung Galaxy Note 7 and, like you, reading teaser articles about the forthcoming rumoured new Nexus phones from Google (although apparently manufactured by HTC).
Again, like you, I will wait to see what Apple announces first and wait to actually see the new Nexus phones.
You mention that Apple used to be the underdog, presumably indicating that they no longer are? I would take issue with this in one respect; recent figures give Android around 85% market share worldwide, to iOS 14% (1% all others), so could one not argue that Apple is still the underdog? Okay, they are a very rich and successful company, so not an underdog in those terms.
What gives me pause when considering Android is, as you mention, the fragmentation and often very slow OS update cycle, unless it is a Nexus. I taught myself to write software for iOS devices a few years ago, when oddly enough at the time I owned a Galaxy Note 4. I also looked at writing for Android, but the fragmentation meant I would have had to write for the older versions if I was to stand any chance of getting a reasonable audience for my apps, whereas with Apple you are fairly safe writing for the latest, but one, version of the OS.
This strength of the iOS system, the fact that the majority of users are on the current (or very recent) version of the OS, is what gives rise to the majority of app developers writing for iOS first, or even exclusively. Even Google! I don’t think there Gboard keyboard is available for Android yet, although it has been on iOS for months.
Another Apple strength is the increasing close links between the related operating systems, watchOS, iOS, macOS (currently OS X) and tvOS. The Handoff service that allows me to start with an app on my iPad and seamlessly carry on with my MacBook. Is it perfect, no, but where is the equivalent for Android?
So, I will wait to see… I lust after the Note 7 hardware, which has features the iPhone probably will not have for another year, but will probably get the iPhone 7 to maintain the strong ecosystem I enjoy.
Good article by the way. :)