And now for something completely different.
I rarely need to update the way you all are talking about here, so I don't really do this, but here is an idea for you. (It uses part of AC for a different purpose than was intended, but that should not interfere with current workflow since I doubt many people use this part at all).
Let's take James' original example: you want to add "PVD and right ICA stenosis" to the patient's PMH.
Go the the patient's chart, summary page, and on the right side, use the "Alerts and Directives" section. Click "Add/edit" and in the window that opens, click "Add new", select Level "high". Under "Name" put "PMH" (or if you want, just type any symbol) and under "Details" put "PVD and right ICA stenosis". Save it and close the chart.
The nice thing is that when you go to the patient list and select the patient (presumably at their next visit), that box in the bottom left turns red and includes "PMH: PVD and right ICA stenosis" which:
a. is nearly impossible to miss and
b. can be copied and pasted into the chart at the next encounter.
Yes, it is a few steps, but not terrible. And as I said, that red box at the bottom is far more visible and less likely to be missed than the yellow boxes or flags.