I agree with your observation. The markets are certainly changing and that is to be expected in this industry without question. My personal opinion on it is that Microsoft and Apple are looking to expand their cloud services and turn as many products as possible into subscriptions, which I still cannot justify for my personal use. This model probably works well for some users and students with discounted education pricing on products, however with the industry I am in a perpetual license makes more sense at this time. I prefer my software not need to validate over the Internet each time it is launched to determine if it is authorized to run or if it is not. It simply adds a level of complexity that I feel is not needed and a potential for failure (although I admit, rare).
You are correct that Apple is trying to capitalize on the Apple Music subscription, and as a new generation of users adopt technology, this will probably become the norm. Showing my age, I still purchase CDs and I subscribe to Apple Music. I do find some cloud services provide value and as long as they are not holding my business data that is relevant to my well being, I don't mind to use cloud services for photos, music, and sharing non-sensitive files.
I am just not ready to jump fully on board to cloud services that provide functionality that a local machine or network can provide securely and is not at the mercy of a DDoS attack or other Internet outage. Cloud providers for some products also have a tendency to make an exit strategy complicated and difficult.
OS X (or macOS if you will) and Windows 10 have certainly matured to the point to where they have become very reliable and stable, which is very welcome from the MS-DOS-based Windows 95/98/Me days. Windows NT 4.0 raised the bar with some notable drawbacks (no USB support or FAT32 support when it would have been very useful) and as Microsoft has matured the product in Windows 7 (although I feel that may be intentionally neglecting it now) and subsequently Windows 10, it continues to be a very stable and reliable product. Although I disagree with some of the decisions Steve Ballmer made when he was running the company, and I don't know if he had a hand it in or not, but the company was much more privacy-oriented when he was at the top. Since the new CEO took over he has changed the direction of the company, made some clearly positive changes, and some may he saved the company in many ways, churning out quality hardware products (after a few misses) and launching a successful Windows 10 Upgrade campaign. It does disturb me that Windows 10 is just so leaky by default, guiding you down the path of it sending a great deal of data back to Microsoft without explaining to you what its intentions are with the ill-described "Express Setup" options. I hate to say it as I have always had a great amount of respect for Microsoft and their productivity, server, and Windows products, this sudden shift into making Windows 10 a data-gathering and marketing tool has tainted my opinion of them and their respect for privacy. As once the de-facto standard for business desktops and the inherent trust that comes with that with keeping corporate data secure and private, they have sacrificed that image and trust with the default options of a Windows 10 installation.
I do use Windows 10 Enterprise and Windows 10 Enterprise LTSB 2016 and they are quality products. My only complaint is for Microsoft to respect users privacy by default and make all other features that rely on sending data back to Microsoft an opt-in function.
I have used Microsoft products exclusively since the MS-DOS 3.11 days, and was never really exposed to Macintosh hardware until they switched to Intel processors as most of my work revolved around x86 applications. After Apple made the Intel switch, I developed an interest in the Macintosh and OS X, and Apple has, IMO, perfected the multitasking capabilities of a desktop OS with their superior Trackpad technology and Multitouch combined with the gestures that OS X supports superbly. In the end, it gets down to what one is used to. I am not a gamer, which Windows is superior at, and rely on multiple operating systems and many Terminal/UNIX-based programs to accomplish my work, and OS X works great for those tasks. I am also heavily invested in VMware Fusion, Workstation, ESXi, and vSphere, and these products can be successfully managed with OS X. Network and *NIX operating systems benefit with the native ssh client in OS X (knowing that putty is a quick and small download), it is nice to have it there ready to use, along with vim and other UNIX commands. We are at an interesting time in computing - Apple embraced Touch with the iPhone then iPad, the Microsoft bet the company on it with Windows 8 and didn't quite get it right but they haven't given up, and Apple is still sticking to their original idea that touch is just not feasible on a desktop or notebook computer. Thus far, I have to agree with Apple although that may change in the future.