Unless there is a specific niche software that is only on windows, you shouldn't have issues out of the box.
Some games have some compatibility issues, but it is getting better everyday.
I think the biggest hurdle for many people is that they are so used to Windows that it is daunting learning a new way of using their computer.
But once you get over that hurdle, it is frustrating going back to Windows. The amount of ads and pop-ups in Windows is criminal.
Try to use a user friendly distro. I use Kubuntu (Ubuntu with KDE plasma) and it is great.