Engine
Easy to tell, just keep looking at your power rating after every oil change. Once your engine has 'run in' on a new car (200-400 miles), you'll be at 'peak' power, everytime you change your oil the engine should go back to that same power figure. When this peak power figure starts to fall after each oil change, you know it's time for an engine rebuild.
Chassis
More difficult to tell. Different peolpe have different indicaters they use to know when a chassis needs rebuilding. Look out for things like the (driven) wheels spinning in a place where they never used to, or the car spinning or back end 'snapping' in places it never used to.
Obviously, any negative changes to the setup or changes in driving style / speed will have similiar affects too, so you need to be consistent with your driving.
If everything is the same - setup, driving style, corner entry speed, apex speed, throttle etc etc and the cars starts to react when it never used to, this is an indicator that a chassis rebuild maybe due.
But, different people have different opinions on this, this is just mine.