Well, there are probably some subtle details which I'm missing, and may be you are totally right.
The way it looks to me is as follows: They are "happy to break kernel ABI compatibility" because the repository is monolithic - they break ABI, they immediately fix user space apps.
E.g. NetBSD time_t 64-bit commit: https://marc.info/?l=openbsd-cvs&m=137637321205010&w=2
They patched the kernel:
sys/kern : kern_clock.c kern_descrip.c kern_event.c
kern_exit.c kern_resource.c kern_subr.c
kern_synch.c kern_time.c sys_generic.c
syscalls.conf syscalls.master vfs_getcwd.c
vfs_syscalls.c vfs_vops.c
and fixed broken user space at the same time:...
sys/msdosfs : msdosfs_vnops.c
sys/netinet6 : in6.c nd6.c
sys/nfs : nfs_serv.c nfs_subs.c nfs_vnops.c xdr_subs.h
sys/ntfs : ntfs_vnops.c
sys/sys : _time.h _types.h dirent.h event.h resource.h
shm.h siginfo.h stat.h sysctl.h time.h types.h
vnode.h
sys/ufs/ext2fs : ext2fs_lookup.c
sys/ufs/ufs : ufs_vnops.c
...There is no "transitional" stage, when the kernel is already patched, but no user space apps are ready for those changes yet. It all happens at once.
-ss