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I prefer Railroad Tycoon 2. (Also Try searching for OpenTTD, Better than both and its free)
Don't expect to play any of them without issues, RT2 has the fewest, RT3 requires downloading non-default confguration files (you can find those in the forums) and SMR has a memory issue, that causes crashes, but can be fixed by modifying a single byte of the exe or downloading it from the forums, but it's still a good idea to turn on autosave in the options.
I would get the bundle, it's not too expensive and you can then play any of them anyway.
RRT2 is still great and deeper, but it takes a bit more effort when I want to play it, which is hit or miss.
Edit: BTW both RRT2 and RRT3 worked fine for me on Windows 7 64-bit
The thing is, it's a game I simply cannot take seriously at all.
RRT3 added 'naturally flowing resources' which ruined the strategy side of the series imo. Towns built up on their own, receiving resources if they were near a river for example. Many times you could load up on something to deliver where it's needed, only to find that need is now worthless when you arrive, because resources came by a river before you got to the town.
That right there, developers have taken it a step further nowadays with gooo ALPHA!
Came here though to see what ppl thought, nothing has caught my attention like RT2
great game and not suprised others aren't as good :D
they really need to just tweak the graphics an inch and make it 3d glasses ready, if it isn't already :) is it already? O.O :D