Although Linux filesystems are not immune from fragmentation, there have been recent developments that greatly reduce fragmentation. Ubuntu 10.04 uses the new 'ext4' filesystem, which writes files (even very large ones) to disk as a contiguous block. This avoids fragmentation completely in most cases. The ext4 filesystem also has a journal, which marks unused blocks, so that disk checks run much faster.
I typically install my operating system on a separate partition from my user files, so disk cleanup isn't really needed either. This has another advantage, too. When I want to install a new version of the OS, I can do a clean install without having to back up any of my data or settings. This makes upgrades faster and more reliable. However, I still have to reinstall any custom applications. I do this manually, but of course I could write a script (or just a text file) to handle the reinstallation. But I'm not a programmer, so I avoid doing that.
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