Hey Geezer.
I've never actually done this. But it seems easy enough, now that I know HOW... as long as the rubber valve stem is the right length to both be able to depress the stem coming out of the top of the aerosol can... and seal tight against the top of the can at the same time.
I wouldn't be concerned about weakening the can, either it can take the pressure it was designed to take, or it can't. I'd guess that all cans are engineered to be able to take far more pressure than what they actually have when new. Manufacturers hate law suits so they mandate safety margins. I wouldn't be worried about that. I would however, be careful not to fill the can with more than about 90 psi; well below it's normal pressure from the factory.
But needless to say, if I filled a can just once, I'd assume it would be able to spray out all its contents with just the one recharge.
Concerning the valve, I assume you mean the tube coming out the top of the can? I suppose if someone got klutzy, they could indeed booger up that tube. But either it works or it doesn't; and since I would have thrown the can out anyway, I have nothing to lose by trying.
I hear what cher sayin' about the rechargeable sprayers. But I was just talking about how to deal with the 30 plus cans of various things I have setting around the garage. Seemed like a good idea.
I would be concerned however, what regular air might do to the contents of a can of paint. If I'm not mistaken, I believe cans are normally filled with something besides regular air. Who knows. But atleast I'd be able to finish using a can. Storing it long term afterwards might be a different story.
Thanks for the input.
Gary