Knowing that Voldemort will be after Harry, it was Dumbledore's duty to ensure The Boy-Who-Lived has the best magical tutors possible. Instead:
1. He placed Harry with magic-hating muggles who did their best to 'squash' magic out of him. Dumdledore even admitted in the end of Fifth year that he knew about the abuse and did nothing to stop it. The result - Harry knowing nothing about wizardling world, abused, with low self-esteem, with a habit of underperforming (he was punished if he got better grades than Dudley).
2. He kept hiring bad Defence Against Dark Arts teachers. Quirrell was possessed by Voldy, Lockhart was a fraud, 'Moody' was Polyjuiced Death Eater, Snape hated Harry with a passion. The only competent DADA teacher was Remus Lupin. In fact, because of Umbridge Harry was forced to waste his time TEACHING Defence (instead of learning).
The only 'training' Harry had were his adventures, and that's hardly enough to prepare the teenage boy to face the Dark Lord.
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