'Solving' a failure of vision
Is my proposed solution of making Beyonce and Jay-Z live as Cuban peasants for a year completely off the table? I'm sure that would do wonders for them. Assuming they didn't forget their place and decide to criticize the regime, of course, in which case wonders would be done to them.
For all the liberal talk about "compassion," this is a failure of compassionate vision - an inability to understand what's actually happening to real people, beneath the cloud cover of politics and ideology. I'm not sure how you "fix" that. Most celebrity Castroites are either stupid or vicious; sometimes both. The dumb ones believe all the socialist rhetoric. The vicious ones are in love with the romance of collective power, dazzled by the Maximum Leader and his breathtaking vision. Some of them are fashionably anti-American, and swoon over anyone who vexes the Great Satan. And you've got the well-meaning but naive types who imagine they're "engaging" the Cubans by swanking through Havana on the VIP nightclub tour.
I'm not sure how to correct any of those attitudes, but I'll take a pass on any further "champion of society" moral posturing from those who indulge one or more of them.