This answer uses the smoothness of the system so I'm not sure it's the most general.
The high school physics setup describes a system that is
Time reversible. If q(t) is a trajectory, then q(-t) is another solution. In this case a ball that starts from rest and slides down the hill.
But staying at rest at the top forever is another valid solution to the initial conditions (at top, v=0)
These are two different solutions for the same initial conditions, violating uniqueness. Now I invoke the smoothness of the slide to say the solution must be unique (this is a standard theorem depending on Lipschitz continuity, which we have). Since permanent rest at the top is a fine solution, the other trajectory must be something else (one that takes infinite time). This is in contrast with Norton's dome which has a cusp at the top.
Poor nephew!
If the top of the slide is parabolic we get an example where traversing
a finite distance takes infinite time.
Let's suppose we trace the parabola y = x^2. When we start at some (x0, y0) we must have kinetic energy = gravitational potential energy: 1/2*m*v0^2 = m*g*(-y0). Notice that the velocity is proportional to the square root of the vertical distance remaining.
What does it look like when we're halfway there? Now we're at position (x0/2, y0/4). We have used up 3/4 of our kinetic energy. Now our velocity (v1) is given by 1/2*m*v1^2 = mg(-y0/4). After substitution v_1=v_0/2. Ah.
The key is to notice that the remaining parabolic trajectory, starting from (x_0x0/2, y_0y0/4) is exactly a scaled copy of our original situation. We have climbed, but we haven't made any progress.