De-registering parent style sheet css recommended?

This is not a very smart thing to do. As you noted yourself, you’ll have issues when the parent theme is updated. Moreover, the parent theme might have secondary stylesheets that depend on the parent style (third parameter in wp_enqueue_style). There might be javascript that assumes it’s there. In other words: it will take very thorough analysis of the parent theme to make sure you’re not messing up something.

The upside is small. Yes, you’ll have one file request less, but that’s not a lot these days. Even a big css file usually is smaller in terms of kb than the images. And browsers won’t choke on multiple css layers. Javascript is a bigger concern.

Simply said: it’s not worth bothering about this.