what if the update causes a conflict with another plugin/theme? since I am not there doing it myself, it will ruin my site and I won't know until I go to my site.

I have 7 of my own sites I run, they all have Jetpack. It takes me no more than 60 seconds to update jetpack. Even if they all had their plugins with updates...It would take me no more than 5 minutes.

I check my websites in the morning. how many do any you have that you can't spend 5 minutes in the morning updating?