Perhaps some Mac users can recommend software.
As to your original question, it is certainly feasible to do a positional search within Chessbase for opposite-side castling, whether or not there were wing attacks that followed.
If you know the format (pgn, etc.) someone could shoot you such a file.
I'd tend to find older games more useful for any inexpert student as such games usually seem more comprehensible.
I am ranked about 1400. I try to play through a dozen or so masters' games a day using this website and chessgames.com. I do not have any chess engines and am limited, I think, because we have a Macintosh household.
In reading a book by Keres on the middle game, he said that he and his friends in elementary school would play a hundred games after school and he learned about attacking and defending the king with castling on the same side, on opposite sides, queen-side attack, and king-side attack -- sort of four types of games, with of course misc. attacks being another issue.
What I would like to do is to find a way to search on a group of games pre-sorted for study. Then I could play through a hundred games straight when castling was done on opposite sides, e.g.
I can't think of anyway to do this except to keep track of the games I study in my notebook and then go over them a second time. which I guess would do the trick.