That's so very sad, I'm so sorry Jacey about your dad's tractor and losing your teenage bf, it's so true about the memories and parts of our history that just seem to vanish so fast and when we least expect it too. I can understand your melancholy.
When I was young, I remember losing a close friend of mine. He was robbed and stabbed for his belongings late one night. For months after that I grappled with the loss and how he was such a bright light in the little world I knew and how he had just been snatched away for practically nothing. I was so damn sad and angry too and absolutely helpless to change it. That episode changed me though and it was probably my first real experience of loss from the death of a friend. I still to this day can see his face in my mind, he was such a gentle and kind person, everyone enjoyed his company and then he was just gone. It still chokes me up to this day.
That halloween painting is lovely but I agree with you about the artist relisting it - I don't like that either, I feel that's quite unoriginal and rather poor of character. I wouldn't be able to recreate a painting even if I tried - it just wouldn't sit right with me.