The "Shakespeare/sympathy" thing is a steal from somewhere but I can't remember where I first picked it up. I think it's a solid generalization about his work, though; his dramas are great because you can step inside just about any of his characters and find motives that make them work.

Re: the forced conversion, I don't think that would have been seen as so out-of-line at the time (from the point of view of Elizabethan society, I mean; it was certainly an awful thing for real-life Jewish people who experienced it). I am not that up on the history but I think that Jewishness was seen as something you could "get over" (which is why Jessica can be a heroine and there's no problem with her marrying a Gentile, from the Gentiles' point of view).