One complaint I've always had about FreeBSD port's tree is upgrading outdated installed ports. Typically you need to go by hand and uninstall all the dependancies of a port, upgrade the port, and then reinstall all the dependancies. However, there are a few solutions for port upgrade management. The one I like the best is portupgrade that is available in the ports tree under /usr/ports/sysutils/portupgrade.
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