Here are a couple thoughts from someone who made a wrong decision.
I went a little too light on the insulation for a stretch and had to shelter a few nights. Not too much fun with a ccp. I think when I get back I am going to play around with a DAM as my bottom insulation. That way I will still be comfortable on the ground.
There are places where you are just not going to hammock. Not because you can't, but because you want to. The Huts in the whites and Cloud Pond Lookout a few weeks ago for me off the top of my head. There are also some really great cowboy camping opportunities if you are setup for it.
Oh and don't listen to anyone when they mention the Whites as a reason not to hammock. There is only 3 or so ridge walks where there are no trees. And no one camps up there. It is only something like 14 miles across Washington with 2 huts to stay at and a visitors center to stop at, and a couple of 3 or 4 miles ones. All doable in a day. Most people stay in the huts for a work for stay. If not there are plenty of stealth sites. The Glencliff Hostel has a list of them if you are going north.
I think at least for me, a comfy pad that will work as bottom insulation and ground cushioning would be best. I am finally used to sleeping with a quilt on the ground without getting drafts.
On a positive note, I am in Salisberry for the next hour or so and picked up my cold weather setup. There were a few nights in the 30's lately. Now I am good for whatever comes. I have a line on a waterfall I can hang at tonight if I get going soon.