Check out Jetpack, it can auto-update all your plugins, and has a "Rewind" feature with real-time backups so you can one-click take your site back to a previous state if anything didn't work.
Jetpack has some nice features, the comments form especially. It is, however, very bloated - especially since you'll often only use 2 or 3 features on any one site.
Since Jetpack code is also what we run on WP.com (tens of billions of pageviews) it goes through a huge amount of performance tuning and optimization. The way modules work when you turn them off they don't have any overhead, similar to turning off a plugin. If you were using literally one thing it might feel like a lot, but as soon as you use 2-3+ things Jetpack does it's a lot more efficient than separate individual plugins to accomplish the same task.
I did a lot of WP dev from 2007 to 2011 or so, and I still run my businesses on Wordpress today. I hadn't really dug into Gutenberg yet, but I just played with https://wordpress.org/gutenberg/ and I think a lot of people are overreacting. It's a very big change, but it feels like the right move for the future of Wordpress. I'm sure it's not easy to move a community forward in a new direction when there is a global ecosystem comprised of tens (hundreds?) of millions of websites, developers, designers, users, and entire companies invested in the status quo. I don't envy you!
Also, appreciate you still stopping into HN to chat :)