Honestly, the only troubles I have had beside non-working Nvidia drivers was the dependency-resolver taking forever before aborting due to too many unresolved dependencies. full-resolver takes care of that.

Dialogues? Yes to inform you that some services won’t work until a restart & you are currently using them (e.g. X)

Warning about overwriting config files? Only if you are an advanced enough user to have modified them by hand, and if the update requires a new base configuration.