Dude, that third sightlines is hella too long. First two look bad, but depending on the layout may be tolerable.
One way to fix sightlines is to add tall buildings (after all, downtown city areas have lots of these), and rather than making long, straight roads, make your roads curve and weave around buildings.
Sounds good. My only problem is that if I have one road weaving around a bunch of buildings, it seems weird because most buildings/cities are built on a grid, and/or have more than one way to get somewhere. I'm modeling it off of the Pittsburgh uptown area, near Duquesne University, if you want some idea as to what I'm trying to make.
However, I do definitely want to fix that last uphill. I just don't really know how. I might make some kind of T bone intersection, and block off the long uphill with barriers or a fence. How does that sound?