Thanks for the comments, everyone.

This is what I have thus far; I need to sleep now, so I'll tackle most everything I haven't responded too tomorrow when I resume working on this. Like providing an example of how it looks with the character on it. I made the middle tree and left tree taller and shaded them and have begun work on another middle ground tree. After this I imagine most of the trees will exist more in the background then the foreground.
Do note, the gradient that starts to build up will mostly be obscured by trees. I'll also probably even out the brightness of the snow a little bit from the main path and the back layers. The idea is its in shadow (I also want the area the main character walks on to stand out more) but I think the execution is a little extreme for the idea right now.
As for dealing with the pixel-wide scraggly branches in the trees up front, I'd like to keep them - at least for now - because I feel like a majority of the trees character results from those. But, if it begins to interfere with some of the BG layers further back I'll have to deal with them. EDIT: Unless you actually meant remove the scraggly branches from future trees that would exist in the BG? in which case I plan on doing that.
In fact I imagine I'll probably end up rearranging and altering a lot of the different background features I have by the time I'm done, to help compensate for the backlayer. This is after all the first time I've actually attempted a background quite like this.