I do upgrade my packages from time to time. It's almost always happened smoothly. The few times problems happened were due to 2 reasons:
- the software itself has a buggy upgrade procedure. I probably would have had the same issue with any other distribution, assuming they would contain the latest version
- it's an Arch-specific upgrade issue, but I have so few packets that this happens at most twice a year and it's always documented on the front page of the arch wiki
I have to admit that since it's only my own server, there is no pressure for services to stay up. In practice in the years I've used this setup I've never had an issue because a package was too recent and buggy; it was always a misconfiguration from my part.
I very much like the process of steadily keeping up to date bit by bit, instead of stagnating on a stable base and doing a big bang update every few years. I also like the fact that I don't need to know which version of which release am I going to get, it's always the latest one and it's the one that upstream released.