I think you're headed in the right direction, but the firemen raising the flag is too similar to the 2005 USMC Commem of the flag-raising on Iwo Jima. Besides, without the color, it would definitely lose some of the impact, and the darker tones as you've shown would not show up either. I think you should consider acknowleding the heroic efforts of, both, the FDNY & NYPD. Maybe you could use a dual-date like the bicentennial coinage, 2001 ~ 2011. Chris
The mint has issued worse looking commemoratives than Yours. Keep the faith....with a little bit of "fine tuning".....I think You stand a good chance.
I like the view of the buildings and like the idea of honoring both nypd & nyfd. I am not sure but I think they have like coat of arms for both, and it might work instead of the flag raising. Just a thought, but good work so far!