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.
The problem with 1. is that if you don't store you physical USB (or w/e storage device) somewhere other than your home, if you home burns down or if you lose the backup then your kind of screwed if you do need to rely on your backup. With 2. the only way you actually lose your wallet is if you give out your password (provided it's a proper secure password - not something stupid like 1234) in which case if your dumb enough to give people your password then you deserve to lose your money. It's like if your dumb enough to give people all your bank details don't be surprised if people just empty out your account.
1. Create a super-strong encryption password, stick it in bank or with lawyer.
2. Back-up your wallet online, and tell your loved ones (a) how to access it, and (b) who has the password
No scheme is perfect, but that's reasonable.