Virtual machine software is theoretically a one-and-done purchase, but you know that's not how it works in practice. You typically end up buying an upgrade every year just to get the latest operating system support, whether it's in the virtual environment or your native OS of choice. You might not have to run on that treadmill this year, though. VMware is releasing free upgrades to Fusion (8.5 and 8.5 Pro) and Workstation (12.5 and 12.5 Pro) that support the latest and greatest platforms. The Linux, Mac and Windows versions of those programs can all run Windows 10 Anniversary Update and Windows Server 2016 in a virtual system, including multiple systems on Linux and Windows. On the Mac, Fusion will also take advantage of macOS Sierra features like Siri voice commands and tabbed windows.