With BitAddress, I can see you kinda have to choose, I would rather keep my private key unencrypted (offline that is) than have it generated by RNG and encrypted.. (I hear great things from great people about the Armory wallet used on an offline computer, perhaps that is worth looking into)
Also, why TrueCrypt? Isn't Gpg more suited for this?
I think last time I looked into Armory it was windows only? Doesn't it also fetch the entire blockchain? I already run Bitcoin-Qt so maybe that's why I started exploring other options. But I'll take another look...
As for Truecrypt, I'm just using it to encrypt a drive. I'm not familiar with Gpg or encryption standards in general really. Why would it be better?