I read the book and have seen the movie twice so far.
Gary's relationship with Tommie was really about power,control and manipulation, even more so in the book. Gary, especially in the book, was a borderline psychopath, BUT, the tenets of the relationship remained the same in both the book and movie. Based on the movie version, Gary had at least SOME feelings for Tommie, and enough self awareness to realize that he screwed up in the end, and made it worse for her. Plus he missed a massive crush on Tommie's part. The book version, while Gary was a real ahole, still would not have killed her.
Gary's brother disappeared when he was Tommie's age. The brother was sleeping behind a gas station, nowhere near the location of the cabin.
Also the post thing was partly metaphorical, it was the final act in giving the cabin to her, remember he left a note on top of the post.
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