As much as I love FreeBSD, it has its rough edges when it comes to daily use. And an upgrade, while much smoother than it used to be in the "make buildkernel; make buildworld" times, is still lacking and can break the system.
The saddest is that FreeBSD is massively underfunded. They still manage to do great stuff, make massive improvements. If the big corporations like Apple, who made billions on FreeBSD, could just return a couple millions in donations to the FreeBSD Foundation on a yearly basis, which for them would be less than a rounding error, the OS would be in a vastly different place now. But their corporate greed knows no bounds.