I tend to use ports on servers (typically way less than 100 ports, sometimes as little as 20), and resort to packages on X installs (desktops, laptops). Building X and its ilk from ports is not much fun, especially when you run somewhere from 500 - 700 ports. On a ports-based system I run portupgrade every day, on a package-based system (portupgrade -PP) about once a week or even less, since packages are updated much less frequently than ports.
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