I just wanted to update this thread with regards to my wonderful trip to Santiago. I had such a nice time and the people that I met were very friendly! I stayed at Via Emilia B&B in Villa Olga. I thought Villa Olga was a very nice area of Santiago with nice homes/apartments, restaurants/bars in walking distance and it definitely had more of an upscale vibe (BMW's, Mercedes, etc.). I did all of the tourist attractions that Santiago has to offer minus the cigar factory and I did want to go to Diego de Ocampo but didn't coordinate it well enough in advance.
I went to Liberia Cuesta too inside of the supermarket on Av. 27 de Febrero and bought books by Juan Bosch and 1 on Dr. Joaquin Balaguer. Many of their Dominican books were about Trujillo however, they did not have the book that I really wanted to purchase by Bernardo Vega - Quienes Eran Los Ricos al Final de la Dictadura de Trujillo, which was disappointing. El Tablon Latino across the street from the Monument has this amazing alcoholic Morir Sonando that they serve in a plastic bag. All of the bars and restaurants that I went to were fantastic.