I don't have any advice to offer in this thread. But I do have a retaining wall story.
My elderly neighbor wants to extend his block retaining wall (you can see in the first photo). He needed about 5' of the embankment cut back. He wanted to use some of the dirt to fill in a low area in front of his carport to remove the 5" lip from the gravel to the concrete. We also built a drain into the area in front of the carport. We compacted the dirt and re-spread the gravel afterwards and it turned out pretty good for an amateur.
Bottom line? I got to play dirt-mover-man with the tractor and practice on someone else's property! I have a newfound respect for guys that operate equipment and move dirt. It's much harder than I thought it would be and you really have to pay attention every single second to what's going on all around you. But, it was fun and I helped a friend/neighbor.
Building a retaining wall itself is completely outside of any set of skills I have. Short of calling contractors I wouldn't even know where to start. Good luck.
Attachment 74543
Attachment 74544