For the first images (with X style), it's a question of normals. If you really want 2d, I would suggest to do them Y-style, as the trees. And then by also using the name convention (do a filter by prefix "shader" in Tracks forum) normals are handeled automatically -> hence more uniform lighting.
However, if you can, please go for 3D

. I love you second approach ! How many posts do you estimate for all track ? 500 ? 1000 ?
An average total budget for a track is 1-1.5 mil + another 1-1.5 mil for grass. But there is no actual limit. And even if more needed, there are solutions - what was used to bring Nords into AC.
I'll post more info in the evening when I reach home.
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