Plugin Update Crash Problems

Hey,

So i am helping out a friend with their wordpress site. The problem they are having is that when they update their woocommerce plugin the site crashes. They told me something about woocommerce no longer working with wordpress. They also have 21 plugins that need updating as well as updating to the newest version of wordpress. They are cautious to update everything because they are scared everything will stop working again.

Can anyone help me with this?

Thanks