Kristen T, copyright transfers

It occurs to me that the practical problems of songwriters and performers' copyrights becoming practically worthless because of difficulties in pursuing their receivables through subsequent trading of works, or against intransigent labels, has some resonance with the issue of graphic artist's resale royalties (the laws that forbid alienation of 15% (more or less in different statutes) of a work's appreciation on first sale).  Following a single painting through collectors' hands over the years may or may not be easier than following a song through mergers and purchases; at least the painting is physical and has to be somewhere. 

But the big problem here may be the advisability of musicians' and songwriters' retention of copyrights rather than making one-time sales.  Alan L. Feld, Mark Schuster and I did a destructo job on the resale royalties scheme in our book (Patrons Despite Themselves, 1983) because it forces a transfer of risk from parties generally well-positioned to bear it (wealthy collectors) to parties who should not (poor artists), and I think that analysis is still sound. Resale royalties requirements actually restrict artists' options while pretending to give them something: you have to believe that a painting less 15% of its future appreciation will sell for the same price as it would with that appreciation included to like the scheme, except as a sentimental or symbolic gesture to artists.  (Of course it's essential to recognize that a law like this obliges nothing; it's a prohibition against certain kinds of deals, like rent control.)

I have a sense that entirely aside from the way we collect royalties or might, something is wrong with the market structure, rules, or conventions by which recordings and performances are arranged that causes artists to make bad deals, and I'd like to hear more about this.  My (notional) going-in perspective is that artists are grownups who make business arrangements that seem best to them and that those deals should be respected in general:  what am I missing here, and what could be done about it?  I can conjecture (monopsony power of labels, etc)  but facts are better.

I know it's important to distinguish four cases in this kind of analysis:

(1) an artist early in his career who hopes his new work will sell like hotcakes and make lots of money, but for whom the statistics of the market strongly predict a different outcome
(2) an artist already successful and marketable, with professional help (lawyers, agent, manager, etc etc) who can bargain for a high-value total package, however it is allocated between now and maybe later
(3) the artist in (1) having become (2) years later, who wishes he hadn't made the decisions that looked wise at the time (Rauschenberg at the Scull collection auction, watching paintings he had sold for a few thousand selling for hundreds of thousands and almost coming to blows with the collector, is the famous image of this situation in the art world).
(4) the artist in (1) whose career never took off and wishes he hadn't made the decisions that looked wise at the time.
 The (4)'s presumably outnumber the (3)'s manyfold.

And as defense against the confusion of  (3)'s and and (1)'s, I offer Will Rogers' immortal restatement of the second law of thermodynamics:
"It's easy to make money in the stock market.  Just buy some stocks, and if it goes up, sell it.  If it don't go up, don't buy it!"