Thankfully, for me anyway, "where there's a will, there's a way" has got me through most tough spots in this regard.
I do try and do things legally, and that has generally worked out for most of the older games I love to play. It's been a long time since I've had to go sailing for anything, but I do always reserve that option for cases where there might literally be no other way legally, even when I'm willing to pay money.
I mean, these publishers literally do not give two sh*ts about their old game properties, and yet they will still have expensive lawyers defend their rights to them to the ends of the earth.
This goes for music too. And while I can sort of understand a music publisher or rights owner getting uptight about their music being played for profit illegally, I can't understand why they get so worked up over that music being left over in an old game that only a few hundred (or a few thousand in some cases) people are ever going to play from here on out. So I think those music-in-game contracts do need to be permanent, if only because the number of listeners will always drop sharply at some point, making licensing issues irrelevant.
This same logic can also be applied to cars used in games. At some point, the number of copies sold is going to be so low that it doesn't matter, so let the license be perpetual, dammit. It's just good, cheap PR more than anything, really.
