As far as AnimeFactory releases go, I would suspect that Love Hina came before Pilot Candidate. In looking at the subbing styles and practices, the Love Hina subs are much more "primitive" than the PC ones. That is, no different styles for different situations (PC had different fonts and placement for radio messages, normal dialogue, narrations, songs, etc.), no "released on date xx/xx/xxxx" lines, no OP/ED on some eps, no song translations whatsoever, and no fansubber messages beyond "500Kbps DivX version" / "animefactory@efnet.irc.net" and the like. That would place those releases sometime in April-July 2000.
I have to admit, I have an odd fascination with old fansubs. Call it an artificial nostalgia for an era I never experienced, as I didn't start downloading fansubs until mid-2005. I wish I could get my hands on more ancient DivX3 releases. It's not about "ooh, I wanna stick it to the man and pirate the shows."
It's more about the historical value, and seeing the shows in the same way that people saw them when they were new.