Look, guys. There are the key characters - Irenicus, Bodhi, Gorion... characters whithout whom the game wouldn't proceed. And there are people who are just pawns. Winthrop has no real influence, that's why I am not fan of the "give Cnadlekeep people portraits" idea myself. Tazok...he's just a pawn. Same goes for other Iron Throne members. Elminster... he's just a "awesome character"... I'm surprised no one mentioned Drizzt...
There should be a distinctions.
I would agree for Aran, and *maybe* Gaelan, but if there's a yes for Gaelan, people will ask about Valen or Tanova. Ribald...I know he's a nice guy but he's just a merchant. Selling super-goods can't be a reason for giving him a portrait.
Remember that Arta is just one person and she already prepared tons of new portraits. You requested another 14 that would satisfy you. Now imagine all the time and effort she would need to put in drawing another 14 portraits. Some of them would appear just for one or two talks. Gorion and Tamoko will be included only because those were prepared meanwhile, because Arta felt like drawing Gorion and Tamoko was prepared for EE contest (and even though Tamoko is more like a minor character, she is the one who attacked Gorion, who appear as a kind of guide, later, and who would appear in the and pre-boss opponent - she's way more important than Winthrop, Ribald or even Tazok).
I know you people want more, but v2 is almost here. I'm sure there will be many new portraits that can make you enjoy the game even more