Since his starting equipment is a pair of Short Swords that only he (and every other recruitable Tiefling NPC in the game) can use, I let him keep his ** in Short Sword, yes, especially considering that ALL of his incarnations have it.

And yes, I made his Level 19 Pockets score correspond with the correct 5% per level. Interestingly, his Traps score was 0% as well, which leads me to believe that choosing certain Rogue HLAs automatically set your Traps proficiency to 100% for Bards--but not for Thieves.