Cuba - 50 Years After Revolution

How to Destroy a Country in 50 Years or Less.
Or, "The Seven Habits of Highly Unsuccessful Dictators."
Step 1: Kill or scare away your enemies. This stops checks on your goofy ideas by ridding the country of dissenters and making terror-based conformity the norm.
If you allow a rapid outflow of people initially, most of the professional, adventurous, and capable ones will be gone within a few years, facilitating a rapid decline.
Step 2: Steal and redistribute everything, keeping most of it for your supporters. This accomplishes three goals:
a. It breaks the links between people, their labor, and property. Without property of their own and a minimum (exclusively minimum for most, actually) existence guaranteed, people won't care about building or maintaining anything. You'll have chipped paint across the whole country in a few years. You can force them to work so that your destruction program won't be so obvious, but you won't have to deal with any wealth-building innovation. With this policy, it might take fifty years for your target country to have the same GDP as when you took over. You'll fall behind every other country in the region.

b. By using the stolen money for cronies, you increase national cynicism, sapping any residual initiative they may have been left over from the previous order.
c. It makes the aggrieved eternally resentful which would make any reconciliation much more difficult.

Step 3: Given a choice between a successful, free, mostly just nation and a expansionist, mass-murdering slave empire, choose the latter. You can assure exploitative treatment (As long as you're useful. And then, abandonment.) for your people. As a bonus, you'll be guaranteed of ending up on the wrong side of history.

Step 4: Involve yourself in foreign wars, but be sure to lose every single one. Also effective is intervening non-militarily in other countries and just making things worse.
Step 5: Allow your people to only read propaganda and lie to them about your failures like saying that you didn't meet crop goals because the CIA poisoned your water. It'll buy you a little time to completely destroy the country.
Step 6: It's not good if some people still believe that you have made at least some improvements. Shatter any remaining morale amongst the people by making everything you complained about to justify your leadership worse.
For example: Complain about prostitution and then make your country a whore paradise. Complain about inequality and then keep everybody equally poor except for yourself and your inner circle. Make sure your do this in an ostentatious manner, with lots of parties and women. Complain about foreign influence and then sell your country to the aforementioned evil empire, etc.
Step 7: Finally, try to bamboozle smart but dim-wisdomed people amongst your newly-chosen enemy. It won't help, but it'll provide the rest of your enemy with endless sources of humor and useful examples of hypocrisy.