Live dangerously: deploy on Arch. Then you'll never have to work with outdated anything again ;)
Actually, although I've been using Arch Linux for over two years now (not in production; I'm not brave enough), I've hardly had any issues at all with its rolling updates. The worst was just having to manually delete some Java binaries from /usr/bin when the way it handled Java was updated to allow Java 7 and 8 to exist side by side.
I know a lot of people who use Arch. I myself used Arch for about 10 years. Everyone I talk to has glowing reviews of it, and they've never had any issues.
I stopped using Arch about 3 years ago after my system became unbootable after an update. It was no the first time. In the past, I would be fine reading update notes and fixing the issue. But since I started troubleshooting servers at work, I have zero patience for doing it at home.
One other annoyance that comes with rolling releases is that you should update more often, to avoid making bigger (sometimes conflicting) changes to your system. You end up reading release notes more often. I could turn on automatic updates, but I've been bitten by that in the past.
Arch also encouraged me to tinker, and I was much more likely to make breaking changes to my system than I am now just running Ubuntu. If I had the time/energy to try out new distros at home, I would probably try Nix or something similar, that emphasizes rollback capability.
The thing with "rolling-releases" is that updates will bite you in the ass exactly then when you have absolutely no time to deal with them.
So even if the system boots, it doesn't mean anything because booting a system is only one out of 100+ use cases that you will never be able (or willing) to test after each pacman -Syu..
Actually, although I've been using Arch Linux for over two years now (not in production; I'm not brave enough), I've hardly had any issues at all with its rolling updates. The worst was just having to manually delete some Java binaries from /usr/bin when the way it handled Java was updated to allow Java 7 and 8 to exist side by side.