It doesn't have to be him who is the weakest link in that security chain.
What I don't get from your posting is the second part. Personal computers aren't prone to failure at all. I never had a single HDD crash. I backup my data on a second HDD just in case. It's incredibly unlikely that my data is going to be lost and that the cloud is the only solution for that.
So, there's clearly no compromise for me. Rule is: No cloud, no internet service for private data. And heck, I don't even use any analytics software or other software on my company website that I cannot self-host.