All of this crap will only make it harder to a) make backups and b) restore from backups and c) recover backups should you ever forget your passwords. In the end you'll be dissuaded from making regular backups and you'll loose coins, so keep it simple. Use the built in encryption in bitcoin-qt and store your backups offline on removable media like USB drives. Sticking it online is asking for trouble.
Also remember to make new backups once every 100 transactions or you'll loose coins. Alternatively you could switch to electrum and only need to make one backup at the start.
Provided he uses a long password (20+) with numbers, different cases and symbols he should be fine with uploading it, as unless his pass is guessed or hit by a dictionary attack he should be fine with uploading it to an online storage site. Plus it means that if he has a fire or somehow loses all his USBs he can always download a copy of his wallet.
Let's see to crack the wallet you need a copy of the encrypted wallet + the password
1. Offline backups mean to get the copy of the encrypted wallet you need to physically visit his residence/office and grab the backup disks.
2. Online backups mean you need to access his cloud account. You can take your sweet time doing this remotely. Phishing attacks would work in this scenario.
So IMO 1. is much better.
edit: To secure your wallet in your online storage you have to keep a strong password for you wallet file, your storage account *and* your email account because otherwise a thief could use the forgotten password link to get access to your storage account. To secure your offline backup you only need the password for your wallet file and the key to your safe deposit box/storage box whatever where you are keeping your backup media.