My farm has pretty tough conditions, but I think it is much easier to start seeds in pots in a controlled environment and then later transplant your best and healthiest seedlings than it is to grow straight from seed to tree in the "wild". (The kids liked watching the results in the basement "grow room" when I did trees and Mom did garden plants.)
However, trees have been growing from a nut in the wild by themselves for hundreds of millions of years!
Maybe in your area, your best use of time and effort would be planting your desired seeds too densely. If a huge number make it to 5 years of age and are well-established, then it is quite easy to cull a few of the weaker trees.
If going with the seed plan, I would try to maximize diversity of the micro-environment of the planting locations to get the most trees through the unknown future weather conditions.
My trees usually have to combat drought, so I planted six chestnuts in one of my small depressions. We had prolific rains the entire next spring and summer and all but one of the trees died because they were too long in fully water saturated ground!
I think if you plant a few seeds in the depressions, a few on the tops of the hillocks, a few on the side slopes, then you will have a much higher likelihood of having a significant number of trees make it to the 5 year mark.
Good luck on your ongoing tree projects!
