Regarding Jessy, at the very least you'd need to change it so she only gets half value for "selling" her stuff. That would make it less practical to cycle the decks. However, this ability should really belong to a Merchant character or something. She's really just selling and trading, whereas normal investigators can only buy. Then Philosophy can be an ability that makes a little more sense, like tome-related abilities or etc.
Also, Ben having two .45s is not a good idea IMO. Starting with +8 physical weapons that don't exhaust is pretty heinous, and makes no sense for the character either. Federal Agents are not Grammaton Clerics or characters from John Woo movies. His ability is interesting though.