Every August, a distinguished group of Cuban-American scholars – from Harvard sociologists to moonlighting International Monetary Fund officials – forsake Florida’s beaches and gather in a downtown Miami hotel instead. Their lofty purpose? To gauge communist Cuba’s transition to a market economy and a liberal democracy. As these meetings have gone on for 23 years, it goes to show that quixoticism can swell the hearts of even reasonable men.

There was once a heady excitement to these gatherings of the Association for the Study of the Cuban Economy. Immediately after the fall of the Berlin Wall, Central Intelligence Agency operatives often mingled with the academics, who knew chapter and verse on the baleful decline of Cuban total factor productivity, but were more likely to have slide rules in their pockets than spy cameras up their sleeves.

Since then, most other governments have come and gone, including Cuba’s biggest patron, Hugo Chávez, Venezuela’s recently deceased president. In Havana, meanwhile, the ailing Fidel Castro simply passed the baton to his brother Raúl, who has instigated limited reforms. This was not the transition anybody expected. “Every year, the same faces, much the same words, and nothing has changed!” remarked an old-time attendee with characteristic black humour, but also typical Cuban exaggeration.

It is true that strange cold warlike incidents still swirl around the island. The latest was the discovery in Panama last month of a freighter with some outdated fighter planes and missiles hidden under 10,000 tonnes of Cuban sugar, bound for North Korea. Why Havana thought to dispatch obsolete munitions to Pyongyang for repair, all anybody can say is: weird. Equally weird, their discovery was broadcast in photographs tweeted by the Panamanian president. (The gossip is Ricardo Martinelli wanted to ingratiate himself with Washington – as if commandeering contraband with a smart phone in hand gave the impression of a President Really-On-The-Case.)

Such incidents aside, it is remarkable though how much Latin America has changed over the intervening 23 years – thanks to a boom that, like most of recent history, has passed Cuba by, and how these changes are reflected in the fabric of Miami life, the officially bilingual but ex-officio business capital of much of Latin America.

One of these is the welcome passing of Miami Vice, and not only for stylistic reasons. In the 1980s heyday of the television series, Miami became known for its pastel colours, flash cars, Armani padded-shoulder suits, speedboats and cocaine trade. Today, that business has been pushed overland through Mexico by the US coastguards’ throttling of Caribbean smuggler routes.

Another is how Miami’s Cuban-dominated Spanish conversation has been diluted by other accents – spendthrift Brazilians and Haitian refugees, of course, but also Venezuelan émigrés, whose talk can resemble that of Cuban exiles of old, filled with an anger that to outsiders can seem absurd.

Meanwhile, the Cuban exiles’ zesty language has mellowed into resignation, and its bitterness taken up by Cubans from the island. This became clear during a conference panel of dissident economists, doubtless brave but some of whom only echoed words by Raúl Castro himself. Last month, the 82-year-old grandfather and former general rebuked the National Assembly for the demise of Cuban manners and morals – from urinating in the street to raising pigs in the city, taking bribes, vandalising public telephones and throwing stones at passing cars. Exiles were once called revanchist when they voiced such laments. But times are changing.

Last year this Republican crowd even elected a Democrat to Congress. The old guard are turning up their toes, and the young guard are travelling to the island in droves. Around half a million visited last year, making them Cuba’s second-largest source of tourists. (Did anyone say US embargo?) Even more remarkably, exiles send some $2bn a year to their island relatives.

That makes them one of Cuba’s economic mainstays, which is just as well because mind-boggling mismanagement may well see Venezuela’s oil-fuelled largesse soon reduced to fumes. A case of Miami coming to Havana’s rescue then? Fidel once said, famously, of his revolution: “History will absolve me.” The wittiest rebuke to that was: “Perhaps, but not geography.” And so it has proved.

johnpaul.rathbone@ft.com

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