Hobbit Warrior wins despite imperfect play.
Made some mistakes. The biggest one was probably not going with the sling of buckland (siren curse) and holy might shots as it had +5 DEX which would have given me 4 dex drains by Morgoth before I'd start losing blows with my scythe of slicing. Instead opting for the heavy crossbow. I banished many species of monsters before the fight, too, so the siren curse really wouldn't have mattered much. The buckland sling did more damage, too.