Gee Russ, in one post you reminded me of two of my favorite songs; 'Breaking up.....", the slow version with tinkling, blues-tinged piano accenting every verse, and (with your mention of Eydie Gormet) the song "Goodbye" ('you take the high road, and I'll take the low....). What great tunes. Hate to sound like an ol' fogie, but 'they don't write 'em like that anymore'.
As far as some of our greatest musicians dying penniless, I don't quite view it like that. What they left the world is infinitely more important, long-lasting, and valuable, than their death-bed bank accounts. Still, you're right in that it would have been nice had they gotten the widespread recognition (and comfortable end-of-life) they deserved.
chas
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"Faith means not wanting to know what is true." [Nietzsche]