50+ year Chicagoan here. I have lived all over the northwest side. One neighborhood not yet mentioned is the Lincoln Square area. It is fairly up and coming with lots of two flat brick buildings and new condos. Lots of interesting restaurants, from Indian and German to Kyrgyzstan and coffee house (was just there last week). Lots of singles and young families. Brown line right there on Western Avenue. Gay friendly. Andersonville just east, Middle Eastern neighborhood and Ravenswood just west. Just another thought.