Source vs binary compatibility. Using typedefs like off_t mean you usually don't have to re-write code, but you do have to re-compile everything that uses that type.
Instead, dependencies are built and then installed, then dependents are built against the installed versions and then installed, etc. In the middle of this process, the system can technically be half-broken, because it could be attempting to run older dependents against newer dependencies. Usually this is not a real problem. Because of how pervasive time_t is, though, the half-broken state here is potentially very broken to the point that you may be unable to resume the update process if anything breaks for any reason.