If I call a virtual function 1000 times in a loop, will I suffer from the vtable lookup overhead 1000 times or only once?
The Visual C++ compiler (at least through VS 2008) does not cache vtable lookups. Even more interestingly, it doesn't direct-dispatch calls to virtual methods where the static type of the object is sealed. However, the actual overhead of the virtual dispatch lookup is almost always negligible. The place where you sometimes do see a hit is in the fact that virtual calls in C++ cannot be replaced by direct calls like they can in a managed VM. This also means no inlining for virtual calls.
The only true way to establish the impact for your application is using a profiler.
Regarding the specifics of your original question: if the virtual method you are calling is trivial enough that the virtual dispatch itself is incurring a measurable performance impact, then that method is sufficiently small that the vtable will remain in the processor's cache throughout the loop. Even though the assembly instructions to pull the function pointer from the vtable are executed 1000 times, the performance impact will be much less than
(1000 * time to load vtable from system memory).