I wear a crucifix that was blessed by our parish priest. Later, I was wearing it at a conference with Fr Coropi, and he performed a blessing for any religious articles we may have had with us.
This got me thinking. If I was to wear this crucifix to Rome, and the Pope performed a general blessing for holy items like rosaries, crucifixes, etc, would my crucifix be "triply blessed"?
Yes. If you put an item in front of three different priests and each one of them blesses it, then the item has been blessed three times. If you bring it to 1000 different priests and each one blesses it, then it's been blessed 1000 times. But what does that mean? What is a blessing? What does it do to the item?
It doesn't do anything to it, whether once or 1000 times. The item isn't changed in any way; a medal is not thereby "activated" somehow. A medal is an inanimate object and will never be "activated" no matter how many times a priest makes the sign of the Cross over it, or how much Holy Water he sprinkles on it. But then, of course, that isn't the point of a blessing, to act like the spark of electricity that brings Frankenstein to life. A blessing isn't magic; it isn't a Sacrament, either.
A blessing is an approbation, a sharing of favour, an expression of approval. When a girl wants to marry a boy, she asks her father for his blessing: his approval. If he verbally approves of the marriage three times, rather than just one time, is there a difference? No. The approval was expressed: the blessing was given, the fact that same approval was expressed three times doesn't make it more meaningful than an approval that had been expressed only once.
If you have a medal or a rosary blessed by a clergyman, basically you're asking him to ask God to smile down upon it. Does that do anything to it. No. That sort of a blessing is done to honor God more than to benefit the item.