If I'm understanding the color pattern of plan #2, it looks like your first yard switch (in the dark blue / purple track) is near the start of the incline on one side of the major bridge. That may be within your vertical easement area which is a definite no-no. Even if that particular switch is "level," you still don't want to start your incline with the next attached piece of track.
I have a few ideas for improvements (including relocating your wye), but you didn't attach the SCARM file for plan #2 so anybody could work with it.
Chuck
PS As I was typing this, I found out the my 5th grandchild is being delivered sometime tomorrow (planned delivery). Hope somebody else can help you with this.