I’m doing something like that! The main difference is I am not in an open farm field but just a clearing in a medium-young woods, so I have more forest edge and more shade. My soil is sandy and rocky, free draining but plenty of rain (and snow, which is still melting now). I’m at the very northern tip of Wisconsin.
An example of a naturally occurring guild here is hazelnut shrubs with wintergreen (G. procumbens) and pipsissewa (C. umbellata) growing underneath. That is at the edge of woods with mainly white pine, red maple, red oak, paper birch, and a big of ironwood & balsam fir. So I think once you have shade under larger shrubs or small fruit trees, you could establish something like that alongside blueberries. (These medicinal herbs do tolerate some sun as well.)
Another one is sumac, juneberry, and thimbleberry with some introduced medicinal plants - I’ve often wondered if an herbalist lived here before me. Those are things like yellow archangel, st Lawrence / bundle weed, Veronica / speedwell, lungwort.
Some of my other native medicinal plants that are doing well here include yarrow (which you mentioned), self-heal, anise hyssop, wild raspberry and dewberry (food and medicine!), milkweed, fireweed, wild
rose, goldenrod, prairie sage, columbine, asters, fleabane, bear corn, wild sarsaparilla… I have many others hopefully thinking about germinating out there, seeds I collected last summer and fall. Some shrubs I’m adding this year are plum, more blueberry, hopefully sand cherry if cuttings take, spicebush, and American hazelnut (what I have wild here is beaked hazelnut).
In some cases, I have a guild in mind - like putting the blueberry and sand cherry near a sugar maple, along with sweet fern and wild basil. Others I have not figured out yet! Such as the plums, so it’s interesting to see what your plans are. Are you working from a list of herbs and a list of shrubs & trees you definitely plan to grow, and just need to match them up? Or still developing those ideas of what to grow?