I have worked with all the variants of Microsoft Windows in my 30+ years working in the IT Support industry. There have been many issues for users throughout the transitions from one generation of Microsoft to the next and this has not changed.
Upgrading invariably involves licensing costs to the user. If you have a small business/network of Microsoft systems and are advised to upgrade your Microsoft Windows, this can mean upgrading key software you rely on. So the transition can be costly and not all your applications may work after upgrading.
You will often be unable to upgrade because your computing hardware is not up to specification for the latest iteration of Microsoft Windows. You will have to pay to upgrade your hardware (tossing out the old which still works fine!), or continue with the same system and not receive updates that plug holes in security.
Microsoft is now pushing existing clients to their cloud subscription based services, away from the traditional system of everything being on your device and you only pay once for total cost of ownership. There are obvious security implications for this as well as anxiety around losing access to your data when the "cloud" disappears, even if temporary. This can happen with various applications for example, when you don't renew subscriptions and get locked out of your applications and data.
Apple computers have also gone through iterations for their desktop and mobile hardware and have presented their clients with similar transition issues, although many would argue that it has been a smoother experience.
Nevertheless licensing and hardware upgrade issues remain for their users as does the push towards cloud-based subscription services for proprietary applications. There is generally a much higher cost for their hardware so you want the systems you buy to stand the test of time, if you are prepared to pay the cost of ownership.
Security is often raised as a pro for using Apple platforms but like all the proprietary, closed-source systems, it really depends on what you do on or with these systems and your own practices when it comes to how and what you do with your data and the breadcrumbs you leave behind when you venture into the cloud.
Linux is perhaps the most interesting development in terms of it's history and it's impact on technologies today that rely on software or code, to perform a wide variety of tasks. It is a thorn in the side of the business model that survives entirely on copywriting and patenting software creations. Instead of being copyright software or code, Linux is "copy-left" or in simple terms, you are free to copy, modify and use it without dishing out wads of cash for licensing. It is distributed under an open source license called General Public License (GPL). You can read more about that here but the essential message is that any software built on top of and with Linux, must be distributed under the same license.. free of charge!
But how does that concern you? It should be obvious if you have already paid out hundreds or thousands of dollars for software in your computing life time. It's important to understand there is a solid software platform for all kinds of computing needs, big or small, personal or commercial, which is entirely free.
And I can help you discover this freedom, whatever your software needs are, after more than 20 years deploying Linux based systems for a wide variety of applications.
Android is a product of Google meant for mobile platforms like smart phones and tablets. It is installed on the largest percentage of mobile devices globally and has the largest choice of applications available for users to install. It is based on the Linux operating system, an open source project developed and maintained freely by thousands if not millions, of contributors worldwide.
Chromebooks are a class of cheap laptops/notebooks that run on Google's Chrome Operating system and less so on tablets and desktop platforms. Essentially it is a device that runs everything within Google's Chrome Browser, storing everything under your google identity in the cloud/internet and on the device. It's not a device for running proprietary software that require high performance. So it's OK if you are used to doing all your play, socialising and work within the Chrome browser, but not if you already do gaming, CAD, accounting, creative artwork or multimedia studio creations in standalone applications already licensed to you.
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