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So yeah, it seems plausible that Oscar was a pedophile who abused Terry in 1963. When Terry came home, his mother/Oscars sister found out, and stopped any contact (hence the height marks stop). Terry develops a trauma and focuses on the last event before the abuse (the Kennedy assassination 6 days before Thanksgiving 1963). Oscar is remorseful, develops a drug problem, tries unsuccessfully to reconcile with his family and is forced out of business by his apprentice (either because he found out about the drugs or because there was some abuse pattern there too). In the end he bestows the house to Terry as the only way to make up for it and dies as a broken man.
Sam and her lover had a running thing about the ghost of Oscar. It's why Lonnie came over in the first place, and they continuously try to spot supernatural phenomenons in a not-quite-serious pasttime in the admittedly spooky house. In the end they decide to set the ghost of Oscar free with some exorcism, hence the pentagram. This also serves as a metaphorical letting go of their relationship which is bound to end that same night. or is it?