To the best of my knowledge, the only way you can damage your card overclocking is too high voltage or letting it get too hot. If you're not going to be overvolting, then all you have to worry about it temps. So just start bumping up the clocks while stress testing (Unigine Valley or something), and stop once your temps get too high or you become unstable. It's hard to say exactly what temp is "too high", but from what I've read you want it to be at least <90 C, preferably less than 80 C or so. If you're getting too hot, you can also try increasing the card's fan speed.
bootcher :
There is no such thing as 'too much damage'. A 'little' damage will be enough to make the card useless.
It's entirely possible to be slowly degrading (damaging)...