Yo i'm back to ask which tropico game(s) should i start the series with?
When I first played them, when they came out, I thought 3 was an improvement over the ones before, especially over the messed-up 2. But due to a recent bundle, I revisited all of them and checked them out close together, the streamlining was so stark in 3-5. But then, 3-5 are made by Haemimont, makers of such fine games as Imperium Romanum (the streamlined Caesar) and Omerta (the streamlined Gangsters: Organized Crime). So, revisited, I rate them in this order:
Tropico 1: has the best scenarios and the most challenge. (But has old graphics if that offends you)
Tropico 2 (from a different company than who made 1) retains the challenge of 1 but is otherwise a mess.
Tropico 4 Without DLC, rates over 3. Has some graphical improvements over 3, but also even more streamlining. The DLC scenarios actually have some challenge in them, instead of being baby's first city-builder, but each ones adds even more safety buildings, so the challenge is ripped away even as it is added back in. To the point where, even if you decide to be Godzilla and wreck your city, you still win the election. It's sad, really.
Tropico 3 (from another new company, other than who made 1 & 2). A lot of graphical improvements over 1 and 2. But so much streamlining has gone on behind the scenes of an already none-too-difficult game that it has become baby's first city-builder.
Tropico 5 is a direct copy of 4 with a few more bad streamlining decisions added in and some additional cutsey graphics.
In short, Haemimont is a streamliner developer, and everything it touches is generally streamlined into poo. (See Imperium Romanum, Omerta).