I think Windows works much better with express settings. I went through custom one time. I left everything like it was. Didn't want to change a thing.
It seems to be this, because description is similar: Settings > Privacy > Speech, inking & typing Because I always set the setting in your screen to OFF, under that settings page I have a button with "Get to know me" to enable it later.
But look at the 2nd one. It says "Send typing and inking data....". Isn't it the one in Settings > Privacy > Speech, inking & typing?
I think your question of "sending contacts and calendar details" has something to do with "synchronizing with your Microsoft account". I never use a Microsoft account whilst setup - I always use "local account". So "synchronizing with Microsoft account" is not relevant for me. If you use a Microsoft account whilst setup the corresponding switches should be in your Microsoft account settings in Windows 10 or available via website of your Microsoft account settings.
I guess the first one if for cortana related options as a pack. If you disable everything on privacy and later try to enable cortana, it'll ask you to enable many settings one by one.