Regarding the third pipe: After a little digging I did find this dates May 20, 1916:
I did find a possibility that Mr. McGuire was in a clipping from 1905, but I could not find the actual clipping to which the link referred.
I would assume it would be the same person, beings that he has the same name, and he is a tobacconist from Brisbane. I imagine he might have made pipes as well. The clipping does say he was the tobacconist for a late Mr. Mooney prior to opening the shop advertised. If this is in fact the same Mr. McGuire, that should give an idea of when the pipe was made. During, or just prior to, the 1st World War, I would presume.