Is it significantly different planing out the faces of the joint surfaces on hand hewn timber then squaring the faces on cut lumber? Or is there something else that makes the roughness of the hand hewn timbers more of a challenge to work with?
My wife and I do have some lofty goals, and I am not above admitting that my ambitions are beyond my (current) reach. But, again, we are looking to do exactly what you say; small step by step achievements while taping the resources we have available to us and taking the time to learn how to do what we need to.