Trigger when Hot key is down for more than X seconds

Questions & Suggestions
1

I want to know if it’s possible to triggers actions when I’m pressing a specific hot keys for more than, ex.: 3 seconds.

For exemple:

CMD-V = Paste
CMD-V Down = Paste In Plain Text
CMD-V Down for 3 secondes = Paste in Plain Text as Smart Quotes

2

You can have a hot key triggered macro that triggers when a key is pressed and notes the time, and then another macro that triggers when the hot key is released, and it can check the time elapsed and do different things.

However doing this for Command-V as the trigger will be problematic because the Paste action uses the Command-V itself which may or may not work (when Keyboard Maestro simulates a keystroke, it tries to avoid triggering macros but it is impossible to guarantee because the the event queuing). So triggering on Command-V and then doing a Paste is probably going to fail some of the time, and adding a delay into the process makes it even more likely to not be robust.