CrossOver is an application that uses Wine to run Windows apps on your Mac (or Linux and Chrome OS). I guess that on top of Wine they add more testing and custom config scripts for each application. CodeWeavers also contributes a lot of code back to Wine (they do most of the WIne commits).

The UI is simple to use. Click Install, type in the application name, then select the application install EXE. Install goes smoothly though you will have to say OK to any sub-installs. After that you have a Wine bottle with your app. CodeWeavers also supports stores like Steam (install Windows Steam in a bottle then use Steam to install games).

My experience installing Dungeons & Dragons Online is here. There were some hiccups, some solved looking at CodeWeavers forums (they have a page for each Windows app with an accompanying forum channel), and others by finding them on the DDO forums. Everything works well (and a lot faster than DDO on my MBP 2015) and I'm confident CrossOver will run other Windows apps well.

CrossOver 19 includes three versions of Wine to support different Mac OS versions down to El Capitan 10.11: 32-bit Wine, 64-bit Wine, and a 64-bit Wine for 32-bit applications. Although you could do all this yourself with Wine that requires a lot of technical skill and patience. CrossOver makes it simple.

Overall, for running many Windows apps CrossOver is a great solution.