Given the imagery of the game, it really is a little silly just how easy it is to "win" Tropico, in the sense that "winning" is an economically productive island populated by people who are willing to keep reelecting you of their own accord. With Political Stability at "Average" and a 0% modifier to export prices, I'm doing just fine. I birthed all of two rebels (I think a third died of his own accord) when a hurricane bankrupted the island at its start, and I finally remembered I could offer them amnesty. Meanwhile, crime is almost nonexistent, nobody gives a shit about liberty, the (3) officers stopped complaining about their wages, and I won my last reelection with 75% of the vote (an island-wide payraise probably helped). 150 of 200 people are over 70% Respectin'. I did have a dock-worker strike, but they started right as a freighter left and tantrumed themselves out right as another arrived, so it's all hunky dory.
For the longest time, I kept winding up in debt, wobbling back and forth from red to black depending on how recently the foreign aid had come in and how much time my teamsters spent scratching their asses. I finally found out that the world economy was in recession, and a 20% decrease in export prices bounced back. I'm still constantly in the red (worse than before even), but thanks to some restructuring, my average industry profits are twice what they were for so long. Most of that money has been sunk into more housing (a Diplomatic Office and development deal with Russia pays for itself after a few Apartments), and a Cathedral and Newspaper (holy crap is it a space-hog).
Next up on the agenda is a massive restructuring of my base-level economy. The bauxite mine is finally running dry, my starter papaya farm is pain in the ass to build around anymore, and there's a pineapple farm on top of the other bauxite mine. Including replacing all those in new locations, I'll add a third farm and a fishing dock, since I might be running out of food, and if that it's more crap to can. I may do all this after building a second lumber mill, since the one has 1000 units of input after an overcorrection in lumberjacking, and probably a furniture factory because duh.
Once all that's out of the way, it's time to build a college to staff this expensive shit I bought (the Immigration Office is a godsend, but unreliable), which will pave the way for a refinery, then a powerplant for a hospital and more entertainment. When your speechwriter, the capitalists club, and Betty Boom all harrangue you in one year about the lack of entertainment, you have one bore-hole of an island. But with the Childhood Museum (finally made the 10 Loyalists happy) and a Cabaret next to the palace, I've run out of powerless entertainment. I have no intention of attracting tourists, but if I basically win the game to that point, I might as well build an airport for the Trade Deals, and wine and dine some hoighty-toighty moneybags. Too bad I already gutted the ruins for my pocketbook.