Yeah I just tried the relax tool, not at all what I'm going for. It just seems to stretch the UV's even worse.
Just messing with moving the vertices manually, as you suggested, this is what I came up with so far:
Viewport Before:
(At this stage, only planar mapping has been applied)

Unwrap before moving vertices:

Unwrap after moving vertices:
(Here I started by moving the upper vertices to line up with the upper edge of the texture, then worked my way downwards, adjusting vertices to get rid of stretching)

Viewport after moving vertices:
(At this point it looks better than before, but still stretchy)

Render after moving vertices (don't mind everything but the cliffs):

Am I being too finnicky about stretching? I'm a bit of a perfectionist, and I like using the right tools for the job to maximize efficiency... Let's take a look at a30's cliffs:
a30 viewport pic:

Notice how the cliff's edges line up perfectly with the texture? Let's take a look under the hood at the UV unwrap:

I'm curious as to what UV technique(s) Bungie used to achieve this result. In the end, the reason I want to line up the cliff edges is because I want it to blend as seamlessly as possible with my ground texture.
SIDE NOTE: From a bit of research I noticed that two different techniques can be used to achieve the blending effect between grass and cliffs. There's "a30-style" (shown above - and this is the technique I'm trying to get my head around) and "timberland-style", which uses two nearly identical ground shaders (base map: ground texture, primary map: colorless 4-way tileable cliff rock). The difference is the scale of the cliff rock map. For most of the BSP, except the cliffs, the ground shader with a smaller-scale cliff map is used, thus making the cliff map resemble a dirt path (with help from brown coloring from the base map). For the cliffs, the other ground shader is used, this time with a larger-scale cliff map and grey coloring from the base map.
That being said, "timberland-style" blending is super easy to accomplish, and a30's technique is a little harder, but in the end they both have different end results, and I'm trying to add as many techniques to my palette as possible...
Any guesses to how Bungie managed to unwrap those cliffs so precisely?