There's no denying that the "it just works" ecosystem Apple has designed is beautiful – when it works. If you want to do something more technical, something that isn't in-line with how Apple thinks their end-users should be using their products, then it becomes very difficult, if not impossible. At the end of the day (and it took me years to realize this), a computer is just a tool. If it doesn't permit me to do what I want, than I should look for a different tool. If the lack of functionality is because of corporate decisions imposed on end-users, all the worse.
I don't worry too much about specific software, because whether I use Windows, Mac or Linux, I will be able to virtualize or dual-boot to another system as necessary. For instance, I've got a program called SheepShaver which allows me to emulate Mac OS 9 and use software/play games that I remember from the 90s. It's cross-platform, so I don't have to give that up when I move to another OS.
The Surface Pro is nice, though. For my money, it's much more powerful than the iPad Pro.