The only legal thing is for a person to make a back-up of legally obtained media. I fully support this right and I fought for it back in the early days of computing {mid 1980s}. I support the right of a person to back-up CDs, DVDs and other software which they legally purchased. But giving copies to friends is a violation of the law. But those who charge money to make copies are boldly in violation of the law.
I think the first one (giving them for free) is a technicality which I don't really think is wrong, the second one I would think is wrong because it's profiting off of someone else's content. At least you see that's more "bold" as you put it.
Neighbors in my neighborhood used to let each other borrow movies we owned. I watched them at my house and then returned them to the owner. Sort of like blockbuster but for free. Is that illegal?
Is it a copyright violation to have people over to your house to watch a movie on your home theater as your guests, or is this considered to be a public presenation without a license? Are you considered to be operating an unauthorized movie theater if say, your son or daughter has 10 of his or her friends over to watch a movie together?