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I've played every iteration of Tropico, and my advice is to buy exactly one of them: Tropico 4. Each release of the game is similar enough to the point that they only offers superficial differences to the last, and 4 has the best flavour combination of mechanical and design decisions to best simulate being a tropical dictator of your very own banana republic.
Outside of a disaster button, most city planning games chicken out in giving the player the tools to be an utter bastard, but Tropico is part of a now rare tradition of comedic cruelty management games (one that included the likes of Theme hospital or Dungeon Keeper). Unfortunately the Tropico games have never got it's own conceit quite right. Oh, you could play the game as a despicable tyrant who burns books, cheats at elections, steals from his subjects and slush the nation's profits into a Swiss account, but all the mechanics encourage you towards being as benevolent and democratically accountable as possible. It is supposed to be a merit of the game that you can be as good or bad as you like, but in practical terms there is no reason to be bad except for the "fun" of it. Said fun is disputable, seeing as how you can't physically see the book burnings. Calling martial law doesn't cause any visible change in how civilians go about their day to day lives. In Theme Hospital, cynicism is obligated through the game design; your decision to help patients with life threatening medical conditions is based exclusively on a cost/benefit analysis of whether it is worth taking on the responsibility, and not in the slightest on whether their lives matter. Being evil had a purpose in game.
Part of the problem is that Tropico always starts with an empty island to do what you like with. The upshot of this is that once you know how to play a Tropico game, you resort to the same strategy, building the same buildings in a specific order, enacting the same few edicts to maximise happiness and profits, and doing all the nice things to prevent sedition or foreign intervention. All the evil decisions make life harder for you for very little benefit. Meanwhile, real life dictators are bad because in their circumstances there is a definite advantage to being that way. Dictators don't begin with an empty plot of land and a reasonable budget, they begin by over-throwing the previous incompetent who ran an established nation into the ground, only to then suddenly realise it is hard to manage a rebellious, oppressed and unsupported people on a shoe-string budget. Evilness is a survival strategy.
I still like Tropico games, because even if they don't really know what dictators are, at the very least they offer an interestingly themed city builder in an attractive and uncommonly seen setting. None of the mechanics are quite on point, but they still make for a jolly, colourful game.
I came to the Tropico franchise with the fourth iteration, and I loved it, and I'm really looking forward to look into the earlier games. The fifth was the first I bought at premiere and at full price, and it was a let down. The era system doesn't really add much. In 4 you go through similar stages, as you cannot afford all the newer stuff in the beginning, only the transitions are smoother (like in real life). The dynasty consists of same gender born as adults with whom you cannot do that much, beside leveling them and have them work some where for a mild bonus. I haven't tried multiplayer yet, but many say it is not really working that well. But it substracts a lot. You cannot place many things that are purely decorative anymore beside two sizes of gardens without varity whereas in four you had all kinds of decorative items like trees, wells and statues, the buildings are always the same, where 4 had a varities of the same building, tourism is more diverse in 5 when it comes to the locations those can stay, but is reduced somewhat in what you can do to make them an environment worth of vacationing to.
This all leads to feeling that developing that island in five is more like a chore simply to make in game money and staying in power, instead of four where you really get a sense of ownership and pride over a well developed island.
I recently purchased Tropcio 3 and its expansion. At first I was pretty skeptical about the game, it seemed like another Sim City rip-off. Then I played it. The game is pretty hard to get into at first, the tutorial does not sufficiently tell you about the game. You kind of have to learn it yourself. But when you get into it, it is awesome. There are a lot of cool things about this game, and you can pretty much lead your nation however you want, simple and agricultural, industrious and reliant on tourism, or have a mass military to keep your power (or just do all those!). It really makes you feel liek your a leader, you are all powerful, and can really have anyone you want shot. However, you always have to please your citizens, and there are many ways to do this, many are quite rewarding. The graphics are quite impressive, and at times you'll just want to zoom down and explore your city, it looks lively, like a real city, with a realistic scale and people attending to their daily buisness. The one problem with this game is that it gets repetetive after you've tried out the majority of the options in this game. However, this a great game, and the expansion is very good. 8/10.
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