A big note on port vs package versions and switching your PACKAGESITE environment
I had FreeBSD 8.2-RELEASE installed. In this case, the ports tree seemed to be the latest stuff, example it had nmap 5.61.t2 while my installed package (not port) was nmap 5.50. When I run pkg_search nmap I see nmap 5.61.t2, if I run pkg_add -r nmap It was already at version 5.50. When I try updating with portupgrade -aPP nmap it cannot find nmap-5.50 on the FTP site. This is because it is looking for ftp://ftp.freebsd.org/pub/FreeBSD/ports/i386/packages-8.2-RELEASE/All/ which only has nmap 5.50 on it. So it seems that ports follow the 8-STABLE versions while your pkg_add is stuck back at 8.2-RELEASE. I think thats a bit strange, because pkg_version -v compares your packages to the port tree, so it says nmap is out of date, but the package is up to date with 5.50 but there is a new port, a bit confusing here.
Sooo, it seems it would be better to upgrade the entire system to user 8-STABLE. Unfortunately its not very easy to get off the -RELEASE version, you cannot simply use the freebsd-update command, that is only for -RELEASE versions (so freebsd-update -r 8-STABLE does NOT work). You have to to a bit of work, basically track a development branch, see http://www.freebsd.org/doc/en_US.ISO8859-1/books/handbook/current-stable.html and http://www.freebsd.org/doc/en_US.ISO8859-1/books/handbook/makeworld.html
You may want to try simply enabling pkg_add and portupgrade -aPP to use ftp packages from 8-STALBE by setting your PACKAGESITE environment variable to the proper ftp url. Edit your /root/.cshrc file and adding setenv PACKAGESITE ftp://ftp.freebsd.org/pub/FreeBSD/ports/i386/packages-8-stable/Latest/ remember to adjust that i386 to your CPU architecture. Also edit in your users ~/.bash_profile (I like bash for users) by adding PACKAGESITE=ftp://ftp.freebsd.org/pub/FreeBSD/ports/i386/packages-8-stable/Latest/.
Many FreeBSD'ers say its simply better to install most of your applications with ports, and only use packages for the really big apps like KDE or OpenOffice... I may tend to agree. I don't really like compiling for hours when doing a software update, but you get newer packages.