You better either get this one absolutely correct, mate or let someone more proficient do it! Right now your picture does NOT represent this class even by a wide, generous margin! The hull is wrong, so is the superstructure. Also, on the latest iteration of the Northamptons I did completely redraw the 5"/25s, so those are the ones to be used. Main turrets are wrong too. As for the Portland specifically, she ad a different (taller) funnel than her sister for most of her career, and she was lost at Guadalcanal in Nov. 1942. If you decide to proceed, I'll keep a close eye on the development of this project. Also, if you decide to draw the Indy as of the New York Fleet Days of 1935, from which event history has brought us several attractive images of her, thanks to her association with one of our greatest-ever presidents, Franklin Delano Roosevelt, I drew the presidential flag for the USS Houston already.
This is a little bit too harsh - your words are not really helpful or encouraging at all. You are not the final arbiter of who gets to draw what. You should be encouraging and helping Navybrat, not insulting him and lording your superior grasp of various trivia over him and the rest of us.
Anyway, to Navybrat's question, I am not really an expert on these ships, but from a cursory glance at Friedman's Cruisers - I would draw Portland as built, Portland in 1942 (during the Guadalcanal campaigns), and Portland at the end of the war. I don't have a scanner with me otherwise I'd send you the drawings and photos from Friedman's. This class is documented fairly well, though, so using Navsource and other websites should be easy.