Yeah it sucks when partitions that were sized 8-10 years ago are no longer adequate. I've hit the "/usr is too small to complete an upgrade" trap myself. When that happened I rejected the installer's partition suggestions and made /usr substantially larger (this is also necessary if you're going to be building large ports, which also happens under /usr).
So far that has worked for me.
Some people would also argue that using an 8 year old device as a critical path in your LAN is a risk in itself. Taking routers down to do upgrades is pretty common in the enterprise IT world.
It’s not just the partition sizing though. The lack of DDNS and clock re-sync are really painful.
Similarly, if fsck -y is frequently required, maybe just run that way all the time instead of failing to boot, or fix the root problem. I doubt many sers are taking block level backups for forensic repair in case they need to hand assemble inodes.
Anyway, I wish them well. I want a simple, correct and rock solid OS for this sort of use case. The three pillars of computer security are confidentiality, integrity and availability. Hopefully they’ll focus a bit more on the latter two things than they have recently.