I hate being forced into new updates. Like MoonShadow once said (and I am paraphrasing): "I like to wait until they have ironed out the bugs with new releases before I update". I've been following that same rule, and only update if it's absolutely necessary. Which is why I never even upgraded to v0.9
That's a good policy. I also do that. You don't need to update from versions older than 0.9.0 unless you're using rpcssl. Most people aren't.
EDIT: Also, are the cold addresses generated from bitaddress.org safe? Most of my cold Bitcoins are stored on addresses (with their keys) generated from bitaddress.org (i.e. the "Bulk Wallet" option)
bitaddress.org's HTTPS may have been compromised due to this OpenSSL bug, which could have allowed a man-in-the-middle to serve you malicious JavaScript.
I recommend not using JavaScript Bitcoin software for anything important.
I created 4 private keys offline in Bitcoin-QT 9.0 via TailsOS. My client never touched the internet, do I need to bring my cold storage online to create 4 new wallets in 9.1?
No, but don't ever run your 0.9.0 installation. When you want to access your cold storage, update to the latest version first.