I haven't heard anything but down-hillish stuff about Gentoo in a while.
FreeBSD itself is usually a painless upgrade unless you do something like 4.11->7.1. The -U switch to mergemaster even makes the tedious part fairly quick on routine upgrades. Handling third party software on the other hand can be a bother at times.
Generally unless things are to far out of date for your needs, have security issues that can be exploited, or bug fixes you need and or desire: there usually isn't any need to upgrade stuff very often. As the old saying goes, if it isn't broken, don't fix it.
Usually I upgrade things every month or so in related batches, just to keep pace with what changes. That way when something big does pops up in /usr/ports/UPDATING, there isn't a dozen of them piled up from last years laziness.... haha
Thou shalt check the array bounds of all strings (indeed, all arrays), for surely where thou typest ``foo'' someone someday shall type ``supercalifragilisticexpialidocious''.
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