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?
Armory's not windows only - works in Linux and I even recently tried an OSX version, but it's not "there" yet. I does fetch the blockchain using bitcoind, so if you've already done that, you're good. I really like multibit - even in the Linux machine I use for bitcoin it works great.
Truecrypt will help if your computer gets stolen, but if you get hacked while it's running (much more likely) then they'll be able to keylog you and get your bitcoins.
Consider getting VMWare Fusion and making a rather hardcore Linux VM to keep your coins in. It provides yet one more layer hackers would have to get into to get your money.