It depends. I think the general rule is to wipe it off and reapply. It only takes a tiny amount to ensure a thin even coating. If I'm lazy, sometimes I don't reapply. But if you want the best cooling possible, I would say reapply after the heatsink has been removed and replaced.
EDIT- misread your post. No. Only if contact between the heatsink and CPU has been lost (for example, you remove your heatsink to clean it, and then refit it back on your cpu).
I don't know the exact life expectancy that thermal goop will remain thermally conductive, but I think it should last for the life of the system.
But believe me, you will eventually replace your heatsink or CPU or take off the heatsink for cleaning once in a while. And if you do, thats a good time to wipe and reapply if you feel it's needed.
Thermal goop actually takes a few hours to reach a peak performance state. If you constantly wipe and reapply thermal goop, your thermal goop will constantly be in a state of breaking in. You may not like the temps during this stage.