lol, the first screenshot looked alot like one of my first maps thou you are missing more bumy terrain and pine trees
to stop your grass from being pure black on medium settings you need to do your terrain lightmaps, do them on low for now.
1. yes
2. yes
3. no

I had alot of trobble with this when me and sofad where trying to get rain into OGT and we where doing rain sounds for the map and it was really annoying that we couldnt mix sounds like genral rain with rain on wooden roof etc

the only way to do it is to pre-mix the sounds with a sound editor then save them as a new sound, and place them on the map where you want them.
you really need to work on your lightmap settings and your lighting settings to make it really dark, at the mo you really just have a black skie, with normal light settings
try just turning down all the colours in your light settings to really dark colours of what they are now, and then in your lgith settings keep shaddow intensity at 1, but make sun and GI light intensity really low. infact you may want to take our the sun (a setting in the lighting settings) unless you want a little light from the moon.