Following up my own post, decided to change out Cascais Citadela for a non Pousada property. Going to try the Fortaleza do Guincho instead-
http://www.fortalezadoguincho.com
And instead of coughing up $600+ for Six Senses Douro, decided to stay down the street at the Delfim Douro. Will plow the savings into a fancy dinner at SS.