Simulating sticky SHIFT key? or holding shift key

I'm trying to simulate Vim's visual select mode.

The idea is that I'd press ctrl+V to "Sticky the shift", move the arrow keys to select the text, and press ctrl+V again to "Unsticky the shift"

I'm trying the following, but it doesn't seem to work. Does anybody have any guidance?

09%20AM

looks like when you run it a second time, you're still Holding the Shift key.
Try a toggle:

Your macro doesn't work for me either. Nor does any variation of using "Press and Hold Modifier Key".

Frankly I don't see much use in this KM Action. For more info, see: