It's important to follow security best practices wherever possible, but you don't want to make things unduly difficult for yourself or lose sleep worrying about keeping up with the latest exploits. In my experience, there are two key things that can help keep your personal server secure enough to throw up on the internet while retaining your sanity:
1) Security through obscurity
Needless to say, relying on this in the 'real world' is a bad idea and not to be entertained. But that's because in the real world, baddies know what's there and that there's loot to be had.
On a personal server, the majority of 'attacks' you'll suffer will simply be automated sweeps from machines that have already been compromised, looking for default installations of products known to be vulnerable. If your server doesn't offer up anything enticing on the default ports or in the default locations, the automated attacker will move on. Therefore, if you're going to run a ssh server, put it on a non-standard port (>1024) and it's likely it will never be found. If you can get away with this technique for your web server then great, shift that to an obscure port too.
2) Package management
Don't compile and install Apache or sshd from source yourself unless you absolutely have to. If you do, you're taking on the responsibility of keeping up-to-date with the latest security patches. Let the nice package maintainers from Linux distros such as Debian or Ubuntu do the work for you. Install from the distro's precompiled packages, and staying current becomes a matter of issuing the occasional apt-get update && apt-get -u dist-upgrade command, or using whatever fancy GUI tool Ubuntu provides.