I think I can shed some light. Prescription prices in the States are not regulated, so really high volume drugs and some others (mainly Viagra which is much cheaper there and is approx $15 a pill here hint hint) are sometimes cheaper. The vast majority of the time drugs are orders of magnitude cheaper here.
The legality of transport across the border I don't know much about, but the 90 day rule seems correct for what that's worth.
The big issue will be access. Prescription drug regulations vary by state, but technically, a prescription from Canada is not legally valid in the US and vice versa. How much money your Dad saves will al depend on how much Viagra he brings across the border because he'll have to pay to see an American Dr.
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