One version of number 1 is possible.Please check my sentences.
What do you actually want to say [STRIKE]with/[/STRIKE]by [STRIKE]it/[/STRIKE]that? :tick:
What do you actually want me to tell with/by it/that? :cross:
See above.What if I modify the second sentence a bit? Would [STRIKE]that[/STRIKE] these be possible?
What do you want to say me by that? :cross:
What do you (actually) want to tell me by that? :tick: