Ok so COMPLETELY Scrapped my layout.. It was time to buy more track, and the original plan I had was not working for me. It took a good day to take down and clean up.
I bought some new wood, which I didn't mind since my old layout was almost entirely comprised of recycled builders wood, and started fresh. It took me a couple days to put together something a little more simple but expandable, in RailModeller Pro.
First pic is the old layout that I got from the Atlas O Layout book... which is awesome btw. I needed to add the outer layer of track, and a few lines.