To make this short. Placing trees (oak trees), should be able to be done in the same manner as placing a farm. I.E. you can setup a grid placement of the trees.
I have found to keep an economy viable in the long term (+20 years) you need to have a constant and large supply of logs. Which means that you need to plant a lot of trees. And it would make a better experience for the game if you can place those trees quickly.
What would be even better, is to make a “tree farm”. A building where you set a grid that expands to make a stand of trees that gets automatically harvested when they reach full maturity. Make it an up gradable building. SO the maximum size can increase.