John Scalzi answers the highly entertaining question of what he would expect his life would have been had he been born a thousand years earlier?
My family was definitely peasants on my mother's side--four generations after the Irish gained independence, the family still owns the land where they were tenant farmers under the English.
My dad's side though, is less known to us. They were Irish for at least a bunch of generations, but we've got a Sassenach last name that indicates someone way back was a leatherworker of some sort. So I might have been part of the medieval equivalent of a middle-class family, with a skilled trade.
In any event, I would have to hope that the many rounds of strep throat that hit in my youth would have been less likely in a preindustrial society where children didn't congregate in schoolhouses and spread disease. Let's assume also that my and my family's tendency toward overweight would be a benefit, or at least much less of a detriment, in an era of uncertain food supply and no chocolate, and therefore some of my joint issues would actually be improved.
There's still no getting around the teeth. The adult teeth come in, but the baby teeth don't go. Even when we're down to just adult teeth, there are too many to fit in our jaws, so without modern dentistry they would be pointing in all directions and causing whatever problems severe bad teeth cause.