Problem 2: might be better discussed in a different forum, but I'll put on my Carl Jung hat and say that the grief you feel is due to the fact that you have personified this tree, and when coupled with Problem #1 there is a sympathetic relationship between you and the tree described by "hurt". Perhaps you feel this way because the tree has no job in its current state; make use of it and you will feel better.
And/or plant an oak tree when you take one down. If you build right out of the one that was taken down, then the new sapling should be as big as the one you took down before your building goes back to the earth.
Or you could do rammed earth.
Why not Pine or Fir in the first place since you feelings are not as strong about them?
I had a clause in my contract (when I cut and designed) - the clause was a 'greens fee' - for every stick in the frame the owner and myself purchased saplings of a compatible variety from the local ag extension. 150 sticks in the frame so we did 300+ saplings in a day back in 2005. 150 on the owner's property, 150 on my parents (as I didn't live in a place conducive to the planting). We invited friends to help and the owner's daughters (middle school age at the time) helped out.
The owner cut the first softwood one this year for a holiday tree, which went in his house, which also has reclaimed timber work I did as part of a farmhouse renovation (reclaimed). It was a nice way to close the circle - and the trees and the barn and interior work will give a long long time. The smaller is to the greater, as the greater is to the whole.
Mo - rammed earth?
What about the worms?