He has a prejudice
Maybe he has reason, let's not jump to conclusions. It could be for the part of his bitcoins he wants ready access to.
Yes I do want quick access to all my bitcoins at all times. If there is some kind of catastrophic news that tanks the price, I want to be able to get out or at least have a chance. And I will add that the price of BTC has gotten cut in half, but I am actually up in BTC "net worth" since the drop from 1200+ to 600. I'm a trader by nature.
Plus paper wallets seem too insecure to me as it's still a physical piece of paper that someone can potentially get access to. With software wallet, you can encrypt and as long as you secure the pw, then one one is getting in there, as long as the encryption holds.
And yes I do have a pw on my Multibit wallet, but that seems weak and anyone can still open it easily and see how much BTC I have even if they can't spend the funds without the pw or private key.
But maybe I will go with TrueCrypt/PGP combo. I don't think I would add winzip on top of that. But I love PGP virtual disks and use them all the time anyway. So put a TrueCrypt container in one of those and I should be ok, as long as I don't get tripped up by some kind of virus/keylogger, which i suppose is always a possibility.