Does anyone more experienced know of a better way to cover this edge, it's pretty high so I stacked two but what looks really weird is the corner. Is there a different method or a different wall that...
A bridge is a great idea. I would raise the land a little so the bridge isn't right on the land so much. You don't have to use the bridge retaining wall but a small slope might look great.
I would keep all the retaining walls at the city edge level with the land- as in don't sink it lower like that. It's to retain the high levels and then out side it can slope is little if you want. :) (it looks like it's sinking)