OMG, I agree with Papipeguy: keep them all. Sell the wife and kids (just kidding. No, wait).
On the other hand, I'd keep No. 3. That is a traditional pipe. It is beautiful. There is nothing else like it anywhere.
You can just about find the other variations with various other carvers. Not No. 3. It is special, and will always be in the hearts and minds of pipe smokers.
I'd keep the Castello 55's first. I'd see if there is anything else you could sell instead of the other pipes. Drive a smaller more efficient car? They're all commendable pipes, but the Castello 55's speak to me most eloquently.
The Occhio will bring the most money in a sale as it is the most valuable. I prefer the ll Ducca as it is my style. I am not a fan of the other Castello shapes.