Agree, this could definitely use a facelift. Grading would fix the problem, however IMO a wall would look great there with a landscape bed from the existing (top steps) to about halfway down the drive. Could do that for about 4k. On the other side just replace the timbers with a paver edge that matches the wall.
Correct me if I am wrong here. But for the wall, I would just run a line on it and cut it where you need to to make sure it is straight and then set the wall in slightly back (to allow enough room for your base) from the drive and put poly sand in the gap. Sometimes we use expansion board (black board for concrete), never used on an application like this..