I remember trying to play this game years ago while in elementary school and sucking hard at it. In high school I came back with a better understanding of it, and this game is pretty docile once you understand it. Combat is pretty lethal to enter into until you have some major cash flow, so your main route to success is to grind out trade and make it as efficient as possible. You can see everything on the map at once, so it's pretty easy just tedious. Get money, get crew, get guns, get violent.
I beat the game with the economy win conditions and while I felt absolutely vindicated for beating it, I was not excited to go back to try for the other endings. It's fun once you're on a roll, but the mechanics gets a bit dry since this is a pretty slim and lean economy/combat game, and is extremely slow until you start breaking into stride.
If you love entrepreneur games, this is a great somewhat generic office time killer. If you develop grudges easily, this will give you great pleasure to beat. Otherwise, nothing too special. Just solid on the basics, not much afterwards. 4/5 stars.