mine started off with the wacom tablet where you see what you're drawing on your computer.. now has moved on to using my older ipad pro with the pencil but he was able to do great things with the wacom!
clipartstudio was his software of choice for drawing on the comptuer with the wacom
depending on if you have ipads you could also look at purchasing the apple pencil (it works for the pro but also some of the other ipad models)