On my spare time, I manage a handful of servers. And even if it’s not really my job, I try to do it well and efficiently. All of them work on Debian because it’s simple to manage. I started using cron-apt a few years ago. I started by upgrading everything automatically, this was a big mistake. I switched to only sending mails on available upgrades and doing the upgrade manually. But this is also quite painful because 95% of the time, it consists in typing “apt-get dist-upgrade -y” and waiting and I have lots more interestings things to do.
I switched from Debian to CentOS because I had the choice between an old 32 bits Debian 4.0 or a brand new 64 bits CentOS 5.3. And I have some scripts that use the great start-stop-daemon tool, which isn’t available on CentOS. The easiest way to solve this problem is to get dpkg from Debian and then try to compile it. It’s likely that it will fail because libselinux (and it’s subsidiary library libsepol) won’t be registered in the pkgconfig dir.