Too bad if you buy this in Canada you're going to jail for posession of loli.
That shirt can be sent to the US with little suspicion, I have a Hinata Daki that got through customs, it came in Dengeki G's, I also have the LNs it depends on how anal they are and what the item is, most official daki's from non-H anime aren't nude save for the really ecchi anime that includes all of the Ro-Kyu-Bu ones, you would have a chance.
Family project isn't loli either, but importing eroge is a risky practice that I wouldn't do myself.