I read through this quickly but only saw a very brief mention of Ian Tyson, who has produced a great six-CD collection of cowboy songs that range from very old to very recent. A couple of my favorites are his version Night Rider's Lament (no disrespect, Art, I've just never heard yours) and Sierra Peaks, but I'd be hard-pressed to even pick a favorite album out of the bunch, let alone a few songs. I guess I do like the first three albums best -- he goes a little too far electric/country later. But they're still worth looking up. I don't recall all the titles, but one (the third, I think) is Cowboyography, one is just Ian Tyson, one is Old Corrals and Sagebrush (that's the first) and a later one is 18 Inches of Rain.I haven't looked for them, but I'd bet there are songbooks spinning out of the albums. Worth a check.
cheers
ddw