Jason,
I am really interested in participating with you and your group. I can't get to my files until later this evening, but have a number of projects using sketchup (I posted some of them on the old forum, but don't know how to access the archived files.) I will find and will post some that show potential for old buildings, design renderings and finished building photos.
My home town has a formal fascade restoration program with matching grants of up to $25K per building for fixing the fronts up. Not a lot of money but it really broke the ice. This fascade program never went anywhere until the cash came up. Now the whole town square is getting involved. Very infectious.
Next week I will be meeting with the council president of a nearby town to help them set up a similar program for their downtown strip. They want to get peoples energy up and photos with some photomatched SU sketches can help (along with a boat load of money of course). Having a historic district helps. I know Jacksonville has a very active historic society, have you talked with them at all??