My problem is I want it all! haha. So now I'm thinking 5 nights. Lv. NJ Sunday am, go up to Portland for 2/3 nights, see what we can see in the area (Rockport, Camden, Cape Elizabeth, Boothbay Harbor) I realize not all of these, but these sound like some of the reasonable choices. then drive down to Ogunquit for the remaining 2/3 nights to check out what is an easy drive from that area, then head home to NJ. What do you guys/gals think of that plan?

If you want to spend time in Rockport, Camden, Boothbay, you should really stay closer to there. Staying in Portland and going to/from those places will take a few hours of each day.If it's just one daytrip, that's not as bad, but you won't get to all those towna and be able to see much. If you were going to do 2 separate trips north from Portland, it seems like a lot of unnecessary back and forth
You can spend a half day in Portland and see other area sights(lighthouses?) on your way back south to Ogunquit.Or if you don't mind and extra stop, stay overnight in Portland . (2 nights Midcoast, 1 Portland 2 Ogunquit)

Pretty much agree with jamie. I would drive to Portland and spend the night and half or most of the next day there. I suggest staying in Portland rather than going further North to break up the drive since its a rather long haul from NJ. Then drive up to Rockland (my favorite of the 3 places u mention) and spend 2 nights there. U can visit Camden & Boothbay from there. Boothbay is the largest and busiest of the 3 so if you're looking for a place that has lots of restaurants, stores etc u might enjoy Boothbay as your base. Then drive South to Oqunquit area for your remaining 2 nights.