It's Apple's decision to have a free trial, not the artist's, so why doesn't Apple deal with it? If Tesco gives you free Kit Kats as part of a promotion, then they don't automatically expect Kit Kat to give them for free to Tesco. If you get a free 1 month trial of Photoshop, that doesn't mean the developers don't get paid for a month, it means Adobe figures it out from their own stock of money.
Without taking sides, and acknowledging the fact that Apple was short-sighted in drawing up the deals with record companies and artists, your examples are not quite accurate enough.
If Tesco gives away a free Kit-Kat, you can be sure that the promotion idea either started from the Kit-Kat's manufactures, or that Tesco is getting a deal from them. In other words, because the promotion is advantageous to both parties, they normally split the losses. In the case of Photoshop, Adobe are discounting their own product, and that is straight-forward advertising, which is part of the advertising budget for the launch of said product.
The Apple deal is a little bit like Tesco giving away Kit-Kats, so Apple expected to split the losses with the large record companies, because they could afford it, and also because they would have recouped the money with the higher royalty rates. In fact Apple, in the long run, was planning to split the risk with the record companies, not the cost.
The problem is cash flow, as always the scourge of any small business. Apple's sound business model fatally assumed that all the parties could afford foregoing vast profits temporarily, in order to reap larger rewards later. it also failed to understand the totally different business model of small and independent music labels and artists, for which time is a major factor.
It's a shame that it took a mega-rich, self-obsessed pop singer to point out the obvious to them, though I am sure they were already considering the independent labels' arguments, put to them before whatever her name is blabbed on Twitter.
xxx