Gaenor gets my vote. Seriously, I was bloody high leveled, when I approached Gaenor. I did not know what he was about, until he started asking for money. First, I felt sorry for the guy but when he was asking for 100 gold, I said no. Then, of course, he got mad, said he will have his revenge. I immediaetly sensed something wrong, so I got out of the place, only to re-enter again to see if he is waiting to kill me. He was not, not even after numerous enters and re-enters, so I figured it was all empty threats. Then one day, when I was leaving the temple he was there. I did not get freaked out by the ebony stuff he had, I thought, he can't be that tough, I bet this will be over in 2 hits or so, like the rest of the "I am so tough" type NPCs. When I couldn't even do proper damage to him, I started thinking "Is my character inadequate, or is he freakishly tough?", but anyways I ran away and figured "exploit time!". So I hired that Imperial mercanery, gave him some semi-good stuff, and after an unbelievably long session of "entering, doing some damage, leaving to heal, re-entering" he finally got killed. I gave the mercanery the Ebony stuff. I remember he kicked some major ass, from that point on.
Brit'sa. She was literally everywhere
Haha, this. Although she was not everywhere. I've only seen her in Jewelry shops.