FreeBSD Rocks!!
Use ZFS.
Take a time to read and study how it works on freebsd.
After you understood its concepts, create snapshots before doing major upgrades, and if something breaks just restore the partition snapshot and you are good to go. UFS has snapshots as well, but ZFS is having its momentum....
Read portmaster manual. I prefer portmaster also, it oftens resolve dependencies problems that portmanager gets confused about. portupgrade is good too, works with packages if you want, it might be good if you want to use packages often. In my opinion if you want to use freebsd you better use sources. Use binary packages if you are out of time to compile OpenOffice that take 8 hours to build and an average 32bits machine and requires 20gb of free space. Maybe X for example, if you know the upgrade is problematic just keep using the old version.
The secret is run a cron job that emails you the output of portaudit and then upgrade these ports from source, which became available much earlier than packages.
I was a long time Debian user myself and switched to FreeBSD 6 months ago and I am very satisfied with the performance, flexibility and features of O.S. .
Enable this line in /usr/local/etc/portmaster.rc and you will have less problems.
# Save copies of old shared libraries (recommended) (-w)
SAVE_SHARED=wopt
Most of problems happen when you compile a port with an older library, and after you upgrade that library the filename changes due to the change in version, the program won't find the library and maybe it will affect a feature or the program won't run at all.
http://www.freebsd.org/cgi/man.cgi?...ropos=0&manpath=FreeBSD+7.2-RELEASE+and+Ports
After the quirks, it clearly outstands Debian in terms of possibilities.