Portupgrade (aka pkgtools) is a tool set for working with ports and packages.

• portupgrade - upgrade a port using ports or packages.
• portinstall - helps you install new ports in a handy way.
• pkg_deinstall - wraps pkg_delete(1) and provides additional features.
• pkg_fetch - fetches packages from a remote site.
• pkg_which - checks which package a file came from quickly.
• portversion - a fast version of pkg_version(1).
• portsclean - cleans ports workdirs, unreferenced distfiles, old and orphan shared libraries, and stale packages.
• portcvsweb - instantly lets you browse change history via CVSweb.
• pkgdb - manages and searches the package database.
• portsdb - creates binary database from the ports INDEX.

1. Look at pkgtools.conf. You'll find many interesting examples there.
2. portupgrade can stop/start/restart services when you like. Add these lines in pkgtools.conf and you'll always have service started after an upgrade process:
   
     AFTERINSTALL = {
       '*' => proc { |origin|
         cmd_start_rc(origin)
       },
     }
3. You can fetch INDEX and rebuild portsdb with one command:
   
   portsdb -Fu
4. Use portinstall(1) and pkg_deinstall(1) as an alternative to pkg_add(1) and pkg_delete(1).
5. You can see a port history in your browser with portcvsweb(1) easily.
6. portsclean -D will purge old distfiles. portsclean -C will clean all 'work' directories. portsclean -L will clean up unused libraries in /usr/local/lib/compat/pkg. portsclean -P will clean up outdated packages.

For more information about Portupgrade, click here and read FreeBSD Handbook -- chapter 4.5 "Using the Ports Collection."