First off, I certainly don't know the answers to most of your questions. I hope somebody can answer the others.
But I believe it's possible a game uses 8 texture layers at some places (not everywhere -- too heavy). I vaguely remember a PC games developer somewhere wishing for the hardware performance for no less than 16 layers. But the multiple layers -- whether it's in separate passes (essentially, pass = geometry setup), or by loopback (same triangle through the rasteriser again so no new geometry setup), or by simultaneous multitexturing (in the rasteriser) -- don't help detail sharpness. They add more complex visual effects: detail, light maps, procedural surfaces (lava, turbulent water, etc.), particle effects, shine, gloss, bumps, reflection, refraction, normal-vectors for really accurate per-pixel lighting calculations, and whatnot...
Detail sharpness is best increased by just bigger (more detailed) base textures and better texture filtering methods. You notice how in those pics the road further ahead doesn't show very sharp detail any more. Anisotropic (non-uniform, adaptive) texture filtering which uses a lot of texture samples would help that -- if the blurring isn't actually intentional for dramatic effect (sense of speed)!
Multi-pass texturing is handled by the API and the hardware when the game wants it, usually the user doesn't need or get to touch it in any way.
All AFAIK which isn't nearly enough