That was when i stopped using the cloud for storing personal stuff.
Fast forward a decade and i've more than had my fill of self hosting stuff, so a couple of years ago i went all in on the cloud again, though with a bit of a different approach.
Stuff that is not really sensitive is uploaded "as is". Yes, that includes our photos. While i don't want our photo library to be "public domain", there is nothing there of particular interest to anybody but my family and I.
For sensitive stuff i use Cryptomator to end to end encrypt data before uploading them to the cloud. It has desktop and mobile clients that allows me transparent access to my encrypted files on the go.
For this reason, I enabled E2E encryption for iCloud. Sure, if you are very paranoid, you can choose not to trust Apple, but E2E encryption on iCloud is seamless, and I haven't noticed a difference since enabling it.
I did the same, but i still use Cryptomator for stuff like sensitive documents and the sorts, much like i would have used an encrypted image before using cryptomator.
iCloud works great, and even if you trust Apple (which i do to some extent), your data is still only safe as long as nobody gains access to your devices. Once somebody has access to your devices, files are no longer encrypted.
The choice of Cryptomator was a convenience choice. I could have just as easliy encrypted files using GPG, LUKS, encrypted disk images or similar, but i would not have been able to access those directly from my phone/tablet in their cloud location, which is something i can do with Cryptomator.
For reference, i have about 4TB data in the cloud (~3.5TB photo library), and a 2GB Cryptomator vault, so it's not exactly the main driver of the operation :)
The Crytomator vault is personal, so i'm the only user, which means that conflicts are rather rare.
I've yet to experience synchronization conflicts with iCloud in my day to day usage, and i've been using iCloud since it was called MobileMe. I even ran with a local cache for a few years, and that never caused a problem either.
