[chacha2]

Why is this all or nothing? There's no reason for it to be completely automated, it could have delegated responsibility to the person most in the know of the situation. That way a member of staff could have talked to them instead of pre-made email.

[manfredo]

This incurs extra labor cost - the whole point of automating a system is to avoid the manual labor. At this point you're no longer making your system tactful, you're just eliminating your system.

Furthermore, it just substitutes one failure mode for another. After a dozen instances of telling people they're getting a new roommate because the old roommate moved out due to normal reasons, how confident are you that this staff member is going to check whether the previous occupant died or otherwise left due to sensitive reasons? Chances are, this same blog post would be written except that instead of "I got this tone-deaf email telling me I'm getting a new roommate" it's "This tone-deaf staff member told me I'm getting a new roommate".