Well, I have dealt with mod making and I'm quite experienced in graphics design. I can say that the mod above would be impossible to reproduce with TOAW graphics system, specially the counters.
The map would be possible, but with lower resolution (the largest Toaw hex tile set isn't as large as this). It wouldn't be advisable though. The problem is that games with custom made maps have a lot more freedom to deal with map elements. In TOAW a set of tile (let's say hills) must work alongside open, desert, mountains etc. TOAW has an editor, most games have not, so that the artist can set the colors according to the specific map region; they don't need to design a LEGO like set that works with any possible combination of terrain features. Also, if you compare hex 3113 and 3011 you see that the railway is slightly different, even if the link the same hex sides. In TOAW they would have to be the same, which creates a pattern like look a little more artificial then the more organic look above. This is the price to pay for having an editor.
As for the counters, apart form having just one set available, resolution and available space inside the counter's frame do not allow this level of detail. The best solution I have seen so far, for figurative counters, came from the link below, but wasn't finished. Since the guy used only silhouettes, the figures have a more generic look, so that they can be used for both sides on the map. And I must say that this guy was patient. I have tried to make some figurative counters, but space is too limited and resolution too low.