Hi Joe.
Since 2.8, Grease pencil was split into 2 things. Annotations for simple drawing on the screen and fully blown ‘Grease Pencil Objects’ for all the fancy stuff.
You only have one type of stroke with the annotation tool.
If you want to use the different brushes you can’t use the clip editor/VSE anymore. However, you can do it by dropping the video clip in as a background on the camera then drawing your lines in a grease pencil object.
Or by adding the video as an image plane in the 3d scene and then drawing the strokes in a grease pencil object.
Hope that helps. Let me know if you’re still stuck.