Jeremy, I'd like to be able to say this area has a simple fix but the fact is this area is the focal point of several planes, all joining at once. The trick is to maintain some grace while making them all meet. I do not like straight, square corners, so I curve things to soften the lines. This look will require you to use round backing surfaces for the sandpaper at times and flat at other times. For instance my flat platen has radius corners. That will make the blade plunge with a curve at the top near the spine when dialed in properly. Then I try to match the choil curve somewhat to the plunge curve.
The only way that this is possible is to have the necessary material in the choil to begin with and that is forged in. So you see that there has to be some planning from the very beginning of the knife.
I have a sequence of steps that usually will allow the material. The first step is strange but if you don't do it, you will have much more trouble getting it all dialed in later so bear with me.
#1: Forge the plunge with a forward angle, as much as 35-40 degrees leaning toward the tip. A lot of us are taught to forge the plunges while holding the blade 90 degrees to the anvil, limiting us to grind the plunge square. I hold it as I mentioned about 40 degrees. This will also set the blade up for a good grind.
#2: When forging and during the rough grind leave material on the bottom of the ricasso (as much as needed, maybe 1/4 inch) and back of the choil to be removed later in the finish grind. When profiling do not grind the back of the choil except to remove possible stress risers.
#3: After heat treat flatten ricasso sides and grind the blade flats. This is when you should dial in your plunges as close as you can to each other with the machine (file it if you need to), again allowing material for the finishing. When the plunges are established, grind upward on the bottom of the ricasso till you get close to your target height. Then you should be able to slowly file or grind the back of the choil taking the choil forward and ricasso up to line up with the plunges. If you have allowed the material for removal, this should settle in the ricasso to the desired height.
#4: Do your finishing. One misslick with the grinder will sure mess things up now. I use files and sand paper backed with files to work in the tight areas.
One point about files. Don't let he fact that needle files are cheap, prejudice you against them. A fine needle file will cut almost as smooth as sand paper so they are nice for cleaning up those last minute belt scratches or blending ripples into a smooth line when hand sanding.