What is the relation between discontinuities and stiffness

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I am trying to understand the effect of introducing discontinuities inside ODE on system stiffness.

simply speaking if we have an equation :

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you can have further look here https://ch.mathworks.com/help/matlab/math/ode-event-location.html [Simple Event Location: A Bouncing Ball]

Now if we rewrite this equations as

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do we expect that the stiffness of the problem becoming higher (of course from ODE solver prespective) means higher chance for numerical errors, especially at y= 0.

any thoughts ?