GP's approach does have a bigger learning curve for those that have never worked that way, but after that the ongoing maintenance is simpler, less time consuming and much lower risk. That probably explains most of the difference in your experiences.
Anyone with some knowledge of Linux/Programming shouldn't struggle setting this up within a few days. And it adds knowledge to the company that's very valuable.
With Gitlab, as with most software, restarting it regularly outside of office hours is the best way to ensure a stable service. Also something SaaS can't do, as they never know when their customers need the software.
Upgrades aren't automated but as the server is only exposed to the internal network (and also not fully exposed there), the attack surface is much lower. Keeping servers up to date isn't hard, and we don't always insist on running the newest Gitlab version. We make sure to upgrade if there's a very critical bug or if we lag too far behind.
It's true, upgrades for Gitlab could be smoother, but we've never had significant down time from it. And while others might say it destracts from day to day work, I (and some others) find it a welcome break from coding.
Taking a actual break works too, I think. I mean, it is a virtue to see good in everything ..
Please, please don't ever do this. Or if you do, make sure you're taking a snapshot of the box every hour or something..
Besides, we already make weekly automatic backups, stored remotely and encrypted. And Gitlab automatically makes a locally-stored backup before each upgrade, which is good enough unless the disk fails right after we discover that the upgrade is broken.
A few days later, drop the snapshots.
Upgrades and backups are way more problematic. A while ago I discovered that backups broke and I had to fix it. I setup automatic APT upgrades for Gitlab, but every few major versions or so a manual upgrade process is required. In an organization where people are less vigilant, and/or haven't setup monitoring of backups, this can easily lead to a disaster down the road.
None of this is particularly hard — for me. But for some others this may as well be black magic. Furthermore all this work is a nuisance, a distraction from what I usually do.