[whpalmer4]

Actually, it's not the project that you click on, but the entire row. Clicking on the row handle (the dot at the left) is what i do for reliable results, though clicking in the name of the action and then on the project will do the same thing at the cost of an extra click. I wasn't able to reproduce the behavior of the specific item you mentioned being grayed out, but by clicking in various places I was able to get a different menu that didn't have it at all.

If after selecting the entire row you are still able to get the grayed out Show in Planning Mode menu entry, maybe you could provide us with a picture to help figure it out, if someone else hasn't chimed in with a description of the circumstances where you should get this behavior (if any). You can pull up the menu and then press cmd-shift-3 (or apple-shift-3) to take a snapshot of your screen. It will end up as a file on your Desktop called Picture <date and time>.

I usually don't use SiPM, preferring instead to double-click on the row handle which will create a new window focused on the project that contains the action I clicked.