On #1: I can't recall ever being asked to make a generalized craft item. It has always been "scepters" or "puzzleboxes" or the like. I suspected it would make fulfilling mandates much more difficult.
On #2: Yes, that is the mechanics, but how do we explain it to ourselves?
I suppose if there are to be Dwarven caravans then they must use draft animals and pack animals. The mountainhome, having settled various new locations in the history file before your seven embark on their journey of colonization, must have already discovered and mastered the concept of using large, surface, animals for carrying goods. To use these animals as beasts of burden, they must have learned how to feed them, and incidentally, breed them. This would lead to learning to eat them to deal with the excess stock. They have obviously not learned to milk them (and yes, some people do milk horses).
So why haven't they discovered the concept of growing, eg, whip vines, since they love whip vine wine so much? Herbalism is a skill your Dwarves can embark with, so they do know how to gather surface plants. Why have they not taken the simple step of planting the seeds, as your seven will do?
One explanation could be that the soil is not adequate for this activity at the mountainhome. I did a little research, and my mountainhome for one of my fortresses does have some badlands nearby, so they have some surface soil. I could not embark there, though. Apparently one cannot embark onto a location which contains an active city of one's own culture. So, I cannot spy upon them and see if they are in fact growing whip vines but just not telling parties who go forth to colonize.