I've yolo'd every major upgrade from debian 8 to 13 without any backups of configs and survived... (dont do that though)

For most desktop systems where you're not dicking around with files in /etc, there is almost no pain ever

For servers, dealing with the "do you want to install the maintainers version of ____.conf", sucks.... trying to remember all the things i put in php.ini is a pain

Probably skill issue