I follow the upgrade instruction every 6 months. Its really not that hard. If they throw a part of the base system out that I was using, then I install the port or convert to the "new way". So far, all has been good.
Frankly, my FreeBSD box has been a bigger pain for upgrades with the "solver cannot solve" for pkg on upgrades, and now with the 10.2 upgrade "pw useradd" is taking over 1 minute per run. Since I'm doing student enrollment right now, its getting to be a little much. Such is the price to use ZFS for home and group directories.
Frankly, my FreeBSD box has been a bigger pain for upgrades with the "solver cannot solve" for pkg on upgrades, and now with the 10.2 upgrade "pw useradd" is taking over 1 minute per run. Since I'm doing student enrollment right now, its getting to be a little much. Such is the price to use ZFS for home and group directories.