In this sentence: 苦学し、何浪もして東大に合格, I can't find the meaning? WhenI search up 浪 via Japanese dictionary, it says 'waves' and 苦学 is 'paying one's own school expenses by working'.
苦学する has a second meaning: "to study under adversity"
何浪も means being/doing many times 浪人(it is constructed with the same structure that 何回も("many times").
浪人 means "waiting for another chance to enter university after having failed the yearly entrance examination" (it can refer to the action or to the person doing this action)
So「苦学し、何浪もして東大に合格」means "Succeed to enter Toudai by studying under adversity and being rounin many times."