I haven’t done this yet but I think I would work in zones or blocks throughout the whole area. So, although the north would naturally have the tallest and densest trees the rest of the space would be worked individually. East side, some plants resent sun on them after frost, I’d make sure they were not on the edge. East winds can be cutting so I might still put some pretty strong windbreaks on the edge there to give protection but allow enough space so that trees needing protection can still get sun if necessary but the area between I would underplant with shade loving species to lessen the wind impact. Once the edge is secured and a protected area has been created then surely mid sized trees would be given space first and then underplant so that the trees still have sun where necessary and the underplanting is designed around each tree. Like I say I haven’t tried this on anything like a large scale but I have sorted all my edges in my small garden and the inside is protected and many degrees warmer on the coldest night because of the protection. And yes I have shady areas, where even my white roses love to bloom and hardy fuschias flower from March to December. My rhubarb does pretty well in the shade too and even small hazel bushes flourish.