For me it's the Peter Principle - update until the app becomes worse than it was before. I don't trust them not to ruin more things in the future and I can't really revert, so that's where things stay.
I think the better option is to update the app until it starts getting worse, then switch to something better. If I was depending on a particular app to a point where losing feature X or Y would be any kind of disaster, I'd be actively looking for a different solution.
Technically, you don't need to connect your phone to the computer. It will do it w/o your intervention. I backup/sync all devices in the family to one computer over Wi-Fi.