You can take the aerials directly from njpb live maps, save screenshots, and line them up in Google Earth as Garmin describes here:
http://www.garmin.com/garmin/cms/site/us/onthetrail/custommaps. This is free and Mac compatible.
But njpb doesn't allow you to zoom in very far. So it would be better to use the full resolution imagery. I explained how to do this for Al here, starting with post #10:
http://forums.njpinebarrens.com/recreation/7446-what-good-topo-map-use-magellan-triton-gps.html
The only difference is that you need to choose NJ 1995 DOQQ's from the dropdown menu "Select Dataset to Download".
My post describes doing all this with GlobalMapper, which is one of those expensive Windows programs. So your assignment will be trying to find a Mac freeware program that can what you need. I just now looked, and I think you might be in luck. The 1995 imagery is available as JPEG files (2007 is only available as JP2 or MrSID files). So that means almost any graphics program can open them, whereas JP2 and MrSID are problematic on the Mac.
The ideal is a program that understands the georeferencing metadata. But worst case, you could just take the JPEG files and drop them into Goggle earth and align them visually, as described in the Garmin link above.
Also, have you looked at my map of New Jersey at GPSFileDepot. I have traced many of the roads in the pines on this. If you enable it at the same time as birdseye, the roads will be overlaid on the aerial image.