This past Saturday night was my first real hammock overnighter. It was a chilly night for Georgia, 32*, but I must say that my setup worked much better than expected. I had a cabin nearby that I could fall back to if I needed, and totally expected to have to because of the temperature, but I was toasty warm inside my burrito all night. My outfit was as follows:
ENO DoubleNest
ENO ProFly
ENO SlapStraps and 'biners (I know, crucify me)
AmSteel 7/64ths whoopies
Slumberjack Telluride 30* synthetic bag
Thermarest inflatable mat
First things first, I know the CrapStraps are junk. On my nightly pee break, I did have to tighten up my whoopies as my hammock was just barely touching the ground. The straps had stretched and allowed the hammock to sag 6 inches to the ground during the first half of the night. I only have those straps because I didn't know any better when I bought them, but I have a new set of straps on the way.

Also, I detached the stock carabiners from the hammock and now store them separately from the hammock for fear of the compression opening the biners and pinching holes in the hammock. Instead, I just leave them attached to the straps and store them in that bag. I know, they're also heavy, so I have some wire-gate biners coming too.

I was very pleased with the coverage of the ProFly. It wasn't raining, but I did have the tarp pitched low to keep the wind down, and I'm fairly convinced if it were oriented correctly, it would keep driving rain out. I made a rookie mistake that produced a 6" tear in the end near the grosgrain loop, but a quick session with a couple strips of duck tape fixed her right up. The tension adjusters on the corners of the ENO tarps are the cat's meow.

My underlayers consisted of nothing more than a pair of jeans, cotton long sleeve t-shirt, and thick wool socks. When I laid in the hammock, I realized I would need a pillow to get comfortable on my side, so I shed my jeans and wadded them up under my head. So in actuality, I slept in a t-shirt and wool socks.

I unzipped my rectangular bag about 3/4ths of the way to form a footbox, but used the rest of the bag as an overquilt. I bought this bag secondhand for really cheap, so I doubt it retains it's original 30* rating. I guess I'm just a warm sleeper.

All in all I was very pleased with the new gear I've recently acquired. My last hammock overnight was in similar weather, but I had the stock suspension, 8x10 blue beast, and a coleman bag I was trying to use as a peapod, no fun. The Thermarest serves the dual purpose of keeping me warm and flattening out the profile of the hammock, making it easier to sleep on my side. Hammock camping is the way to go.