twm, I guess that the legal minds of the big music companies, left these points in limbo, deliberately, so that the actual ruling be made from the judges and courts of the world. A small company can't influence judges or/and politicians, let alone afford a big court case expenses. Dylan's recent CD you mention is perhaps "Stud's Terkel's wax museum"from Leftfield, and there was a reference about this loophole in Uncut magazine. (But not with the details you mention, about this one song left out).
I guess no company willingly gives the original masters after 50 or 70 years. So any quality reissues must come one way or another from this company, or by paying something extra to obtain the masters. I imagine that the composition (music and lyrics) fall under a different law, (the 70 year lawfor the composers and authors) so surely there are some royalties to be paid. I still don't know about the radio airplay time, where the big money is.
And something that just came to mind: is it coincidence that the Beatles released the remastered versions, on the brink of the 50 years? Have they actually reset the clock for their recordings, or is it just a matter of demand for the new better editions that will eventually lead the market away from the "free" but inferior originals?
I also read something that Nick Mason said, when asked why they released the ultra, (not so limited) deluxe boxes of the 3 albums, in 3 formats, plus new vinyl, and the answer was that this is the last generation that will enjoy music from "solid" formats. The decision is taken, and with EMI gone 3 companies have the lion's share of the global market.