Thanks and no worries on the late reply! That was definitely the issue on the test project (duh lol). Upon changing that, the tooltip is indeed coming up there.
After investigating further on my main project, I think the issue was that I was using the config.say_menu_text_filter for something else, which was overriding the one used for the tooltip. After commenting that out and using the correct cases for the words, it works there as well :)