I don't run a server for a family. I have about 7 TB of movies, TV series, and anime. It isn't hard but one of the primary jobs is that it discovers my media, identifies it, and makes it available. When it identifies things incorrectly or doesn't identify them at all and I see 10 of the same thing instead of one with 10 seasons it's a bit of a nuisance.
It is still a relatively first world problem but I wish it did a better job more consistently.