[post written before your edit]
The reason for the difference in the 2nd and 3rd pictures is that LFS has an additional mip bias that can be set per surface type.
The reason for that is because textures that are seen very flat-on (I mean, at an oblique angle to the camera) like road textures, and to a lesser extent walls, need a lower mip bias or they go soft too early [this is certainly true if anisotropic filtering is not enabled].
To say that another way... if you set the mip bias correctly for a texture that is seen flat-on (about 0 or -1) this is too low for road textures. I just had a look in LFS and currently the road textures are set to have an extra -2.0 mip bias.
This issue I've described is (or was) a problem in racing games because the road is drawn so flat as it goes into the distance. But you've got me thinking now because as I expect you know, this is in fact the purpose of anisotropic filtering... to solve this problem "properly" without the "hack" of assigning a lower mip bias to textures that are likely to be seen flat-on.
I'm not sure if this extra mip bias is needed any more now that we have anisotropic filtering... but maybe anisotropic filtering isn't perfect and can still be helped by having additional mip bias?
I think that it should be possible to turn on anisotropic filtering inside LFS, at the moment you can only switch between bilinear and trilinear. Maybe the additional mip bias should only be enabled when the filtering is bilinear / off...
Opinions welcome.