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Mostly legality depends on how a judge interprets a law-and there's no good way, in the US, to get a decision on something that you plan to do. You need to go ahead & do it, be accused of breaking the law, and only then will a judge make a decision-and if he decides you did break the law, you're hung.
If you want an opinion as to whether or not something you plan to do is legal, you consult a lawyer-and hope that the judge will agree with him. (That's part of the problem-the judges don't even agree with each other, at first. Only over time does a consensus emerge as to how the law should be interpreted-so the first people to do something questionable are always taking a chance.)
IMO it's usually legal to transfer the file, but as Rob noted DRM usually renders the transferred file useless. And stripping the DRM for you own use is also usually legal-but transferring the stripped file isn't. (They call it distributing, even if you only transfer it to one person & don't keep a copy yourself.)
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