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Education and financial decline

By 1900, Whipple's various business concerns were suffering a downturn, which resulted in the slow erosion of his family's wealth. He was forced to let his family's hired servants go, leaving Lovecraft, Whipple, and Susie, being the only unmarried sister, alone in the family home. In the spring of 1904, Whipple's largest business venture suffered a catastrophic failure. Within months, he died at age 70 due to a stroke. After Whipple's death, Susie was unable to financially support the upkeep of the expansive family home on what remained of the Phillips estate. Later that year, she was forced to move to a small duplex with her son.

Lovecraft called this time one of the darkest of his life, remarking in a 1934 letter that he saw no point in living anymore; he considered the possibility of committing suicide. His scientific curiosity and desire to know more about the world prevented him from doing so. In fall 1904, he entered high school. Much like his earlier school years, Lovecraft was periodically removed from school for long periods for what he termed "near breakdowns". He did say, though, that while having some conflicts with teachers, he enjoyed high school, becoming close with a small circle of friends. Lovecraft also performed well academically, excelling in particular at chemistry and physics. Aside from a pause in 1904, he also resumed publishing the Rhode Island Journal of Astronomy as well as starting the Scientific Gazette, which dealt mostly with chemistry. It was also during this period that Lovecraft produced the first of the fictional works that he was later known for, namely " The Beast in the Cave " and " The Alchemist ".

It was in 1908, prior to what would have been his high school graduation, that Lovecraft suffered another unidentified health crisis, though this instance was more severe than his prior illnesses. The exact circumstances and causes remain unknown. The only direct records are Lovecraft's own correspondence wherein he retrospectively described it variously as a "nervous collapse" and "a sort of breakdown", in one letter blaming it on the stress of high school despite his enjoying it. In another letter concerning the events of 1908, he notes, "I was and am prey to intense headaches, insomnia, and general nervous weakness which prevents my continuous application to any thing".

Although Lovecraft maintained that he was going to attend Brown University after high school, he never graduated and never attended school again. Whether Lovecraft suffered from a physical ailment, a mental one, or some combination thereof has never been determined. An account from a high school classmate described Lovecraft as exhibiting "terrible tics" and that at times "he'd be sitting in his seat and he'd suddenly up and jump". Harry K. Brobst, a psychology professor, examined the account and claimed that chorea minor was the probable cause of Lovecraft's childhood symptoms, while noting that instances of chorea minor after adolescence are very rare. In his letters, Lovecraft acknowledged that he suffered from bouts of chorea as a child. Brobst further ventured that Lovecraft's 1908 breakdown was attributed to a "hysteroid seizure", a term that has become synonymous with atypical depression. In another letter concerning the events of 1908, Lovecraft stated that he "could hardly bear to see or speak to anyone, & liked to shut out the world by pulling down dark shades & using artificial light".