Anyone with an iPhone or iPad would benefit from having a macOS-based computer. Additionally, the learning curve for a new user is much less steep than for a Windows computer. Apple has updated its OS for 20+ years, however, still maintains the same basic functionality (turn on/off, open/close apps, etc), the same cannot be said for Windows (Windows Vista, 8, 8.1, 11).
If you have one user or 1000's of users (especially using Windows), Windows Server is a no-brainer! The only reason I would suggest going with a Linux server is if you have old hardware (Windows Server is more process intensive than Linux). But, Linux is open-source, so anyone can publish updates/security updates, but on the flip side, malicious people also have full access to Linux's codebase allowing for much easier writing of exploitations/viruses/malware/ransomware.
User and device management out of the box. Active directory is a proven system for doing this and works just as well as it always has.
ADFS providing integration into many third-party applications using SAML authentication. We use this heavily to make user experience as simple and straightforward as we can.
Local DHCP. It's another one of these systems that is very easy to setup and use out of the box and requires very little maintenance, if any. The system is almost unchanged throughout the years and so anyone with server experience can manage it.
Windows Server is extremely complex, and while newer versions have eased the initial setup process, setting up a server is still a very time consuming and difficult task.
The complexity of Windows Server also makes troubleshooting any problems that arise extremely difficult, both in tracking down the actual issue and then resolving the issue. Often times a problem can manifest itself in more than one way, making searching for the specific problem also difficult.
Windows Server is also very expensive, with complex and confusing licensing terms. In fact, Microsoft provides a 32-page PDF guide on Windows Server licensing, which is in and of itself dense and confusing to follow. To make matters more complicated, there multiple different version of Windows Server itself - Nano, Essentials, Standard and Datacenter edition, and each edition has different licensing terms. Licensing terms include items such as the physical processor's cores of the server, how many users will be accessing the server (called a CAL - client access license), and a plethora of other items.
Microsoft's support for Windows Server can be extremely frustrating at times. While Microsoft hosts a very active user forum, Microsoft employees who frequent those forums often provide only stock answers to questions (without actually reading the details) or no answers at all. For more in-depth - phone support can be quite expensive.
Upgrading a Windows Server from one major version to another (i.e. 2012 to 2016) is a frustratingly complex and dangerous procedure, as many things can go wrong during the upgrading, essentially breaking the entire setup. In fact, Microsoft doesn't even suggest doing an in-place upgrade, but to perform a backup of the existing server, doing a clean install of the new version, and migrating the information from the older version to the new version. In general, it is not even recommended to upgrade from one version to another as the risk significantly outweigh the benefits.
I've carefully reviewed the servers and services currently running on Windows Server 2012, and given the opportunity would renew them as is going forward. There are two systems I currently have in place, one is a very large Linux implementation for a large ecommerce site, and one is a very large backup solution front ended by FTP servers running Linux. Neither are well suited for Windows, but the overall network infrastructure is and will be Windows Server for the foreseeable future.
Everything can (and should) be done through the easy to use/navigate GUI. There is no need for archaic command prompt use to administer the server. But, it is there if you have very specific needs for batch files, etc. that are not covered in the all extensive GUI.
It has been my experience that unless there is a flaw or bug with Microsoft Windows Server, you will have to pay extra for support beyond the support web site. That said, unofficial support on the thousands of technical websites makes self-help support readily available to any technician with an internet connection. Microsoft's support website is also fairly robust, but I find using a popular search engine often returns knowledgebase articles more quickly that Microsoft's search.
Make sure that you have detailed processes in place for every server instance you plan to install/upgrade, if possible get the base OS loaded and Windows Updates applied ahead of time, and if using a VM take a snapshot prior to installing each role, as well as along the way.
macOS just makes sense to me. Each OS has its pros and cons.. macOS works for me. It's well designed, intuitive, and efficient. But it's not cheap... well, macOS is basically free, but you need the hardware to run it, and the hardware isn't cheap. Pick the right tool for the job and for you. And even though macOS may not be thought of in an enterprise environment, it works remarkably well if configured properly. Tools like DEP and ABM from Apple enable device management and lock them to the company. Use an MDM like Jamf to push policies and packages. Jamf can also manage accounts and authentication. JumpCloud is another great product for account management. Although it might not be all included in the box, with the right knowledge, you can build a robust and versatile enterprise Mac infrastructure. You can even do zero-touch deployment in most cases with the correct setup. And Apple employs engineers to help you get it set up right.
Windows Server is more cost-effective and skills are easier to find to support the products. The deployment and management of the product can be automated with Microsoft SCCM. In my opinion, Linux seems to be more secured but takes more time and effort to learn than Windows Server. However, there are more Windows Server skills available in the job market.
