I read Little House on the Prairie to my daughter when she was little. I was amazed at what a complete bad ass Charles Ingalls was. With nothing but a horse, some simple hand tools and a little help from his wife in a very short amount of time he built a house and a farm. With just him and his horse he cut an moved large trees and then shaped and assembled them into a log cabin. It is easy to underestimate how hard it is to move a tree, they weigh a lot. We used a tractor with a bucket, couldn't imagine doing it with nothing but rope some pulleys and a horse. He did this while he was clearing land and starting a farm and he his family was being threatened by Indians who were unhappy that white people were building farms in his land.

There is nothing he did that I would not have at least basic understanding of how he would do it but my practical skill would fall very short. Not to mention my physical condition.

You to go back to the middle ages to find lost technology and skills, we can't live off the land they way our great grandparents did. From a practical point of view there would be no reason to go back to the iron age technologically. Steam power is still better than wind power.