So I start with a particle rolling along the outside of a wheel. This can be constructed by setting up a vector function for a circle and adding a constant velocity to one component.
My wheel is going to be moving horizontally with a velocity v_0, so my vector is... $$ \vec{s}=(r \cos t+v_{0}t)\hat{x}+r\sin t\hat{y} $$
Now I want to implement a condition where the particle will 'bounce back' in the opposite direction once it has met a specific angle from the center. This step will change the path from looking like a flattened spring to a bent sine wave. Hopefully these pictures will help illustrate this.

The bottom function is a bit similar to the affect I am trying to achieve, but it is not circular. Anyway, is this just accomplished with a piece-wise function?
It looks like your $y$ period became twice longer. Don't change the period of the $y$ component and everything will be OK. Instead you should take negative velocity $v_0$ leaving the rest the same.
It looks also that your point moves counterclockwise when wheel moves forward. So you need to change $\sin t$ to $\sin(-t)$. When you point begin to move back you should change $\sin(-t)$ to $\sin t$ again.