You're not running enough servers or enough services on those servers, if you don't mind upgrading every year. Honestly, I prefer Debian with the volatile repository to address that problem. I find CentOS pretty good, as well--grabbing a Fedora SRPM or two and rebuilding is usually an easy way to get the bleeding edge version of something without much pain.
You're right, I'm not running enough servers. But I plan to keep my strategy as the number of servers goes up. I like having the same version of OS on the server and on my desktop. I'm a big fan of having everything (configuration, updates, deployment) automated so hopefully the amount of work I have to do doesn't increase linearly (or worse) with the amount of servers I manage.
I will humbly point out that my business (Virtualmin) is the automation of systems management tasks, likewise for my hobby of the last 8+ years (Webmin). And I still consider it an absolute deal-breaker when an OS has a lifecycle less than three years (my usual upgrade cycle is usually 24-32 months...but I like to have some wiggle room, so five years is even better).
So, you're right that there is value in replicating your infrastructure on your home machine and your server, and there's definitely value in building in replicate-ability from the beginning. Nonetheless, the end-of-life of your server will catch you by surprise one day, and some security exploit will mean you have to upgrade (at least some components) under duress. And there's nothing more stressful than doing things under duress on a production server. It'll take years off your life.
BTW-I run Fedora 7 on my desktop and Ubuntu 7.10 on my laptop, and deploy to CentOS 4 and 5 on my servers, and the pain is minimal (then again, our product technically gets deployed on all of those platforms, and many more, so that cross-platform compatibility is part of what we're always testing and working on--I suspect if platform-leveling weren't part of our value I'd be more likely to standardize).
