Picture this: It’s the year 2026, a decade after President Obama’s historic visit to Cuba. A weakened, corrupt Cuban government is struggling with economic reforms and facing protests over efforts to reduce education and health benefits. Its political leaders are still enmeshed in settling decades-old scores.

Cuba almost certainly is going to change. Its leaders know it. Its people are eager for change, and despite political opposition in the U.S., the logic of reengagement ultimately will prove too strong. The question is, how much? The experience of other countries shows that the transition from communism is rarely smooth. Some get stuck halfway through the process.

This is not an argument against Obama’s Cuba policy, or his visit next week, which will be both an acknowledgement and a driver of the change that’s under way. The policy Washington pursued over more than half a century didn’t work. And the U.S. maintains relations with many countries despite serious disagreements.

Perhaps Cuba will be an exception. Perhaps its proximity to the United States, and the eagerness of Cuban-Americans will make all the difference. But a decrepit state-run economy is rarely dismantled without a lot of dislocation, corruption and unhappiness. And Cuba can’t expect a revolutionary leader like Vaclav Havel to appear out of thin air.

Here are a few things to keep in mind:

Cubans have high hopes that closer ties with the United States will give a jolt to the economy. It’s true that Cuban-Americans – and U.S. business in general – are eager to get a toe-hold on the island. Cuba has a generally well-educated population. Underemployment is a huge problem.

A rare public opinion survey conducted last summer for Univision indicates that even while they expect economic changes, a lot of Cubans still would prefer to be elsewhere — particularly young people. According to the Washington Post, 55 percent of those surveyed (and two-thirds of the people under 35) said they’d like to leave Cuba. Granted, saying you’d leave is one thing; actually doing it is quite another. But still, that’s an awful lot of people.

And here is another is another troubling demographic trend: The Brookings Institution reported that the ratio of people not in the workforce (under 15 or over 60 years old) to the working population will increase over the next 15 years – the exact opposite of the trend in most other developing countries.

So, if there are jobs to be done, it’s not clear who’s going to do them.

And if Cuba were to decide on a massive privatization campaign, who is in the best position to benefit? The experience of Russia and other countries shows that the political elites – and their friends – know better than anyone else where all the levers are located. Perhaps they make the transition as the new ownership class. Or as agents for foreign buyers. Either way offers an opportunity to line their pockets.

Most influential people in this kind of system are pragmatists — not ideologues. You manage to stay on top by figuring out which way the wind is blowing, and positioning yourself to take advantage of it.

The same is true of the political system. Politically, communist — and post-communist — parties often prove to be more resilient than you’d expect.

Cuba’s communists are unlikely to simply roll over and play dead. As a matter of fact, they’ve been arresting more rather than fewer opposition figures.

They also are unlikely to maintain as strong of a grip on the island as they’ve had in the past. One worrying implication, suggested in this Guardian article, is that Mexico’s drug gangs will be able to exploit a convenient new route to their most lucrative market: The United States.

Elsewhere, Communist authorities so repressed the opposition for so long that any alternative had to be built from scratch. A Havel or Walesa has been rare. Disorganization and infighting haven’t been. So you have an opportunity to portray yourself as a competent – albeit chastened – manager who knows how to get things done.

As the transition starts to bite, you also can cast yourself as an economic populist who wants to protect things that people actually liked about the old system. The Univision survey made clear that people are actually quite happy with the education and health care systems. Regardless of who ultimately runs Cuba, it’s reasonable to think those programs will prove to be too expensive, and will have to be curtailed.

Even if the Communists lose power, the opposition might well find itself with a conundrum similar to that facing opposition figures who just took power in Venezuela: Social programs instituted by Hugo Chavez, as bad as they have been for the state budget, are far too popular to just whack.

Then, as fed up as Cubans are with the Brothers Castro, you’d probably ask whether they really want their country to become a wholly owned subsidiary of the United States.

Finally, there is the question of justice.

If the communists or their successors manage to stay in power, they’ll be tempted to do whatever they can to stay there — partially because the alternative simply is too dangerous.

An opposition movement will, quite reasonably, want to investigate who exactly was responsible for decades of repression. And they will want to show there is a price to be paid.