I think it's pretty much a given that everyone has different priorities in the gear selection department - if you are first interested in light weight and THEN in comfort, and THEN budget - you will find different answers than if your overriding and only concern is lightweight gear.

My personal priority list is COMFORT and then LIGHT - to which end, I have a Warbonnet Blackbird, two tarps (one MacCat Deluxe, one winter tarp that provides great enclosed shelter from inclement weather), and a collection of underquilts, top quilt, and sleeping pads. I am adding shortly a Momentum weather shield to further protect my underquilts and provide additional wind break for them. My weight for shelter plus insulation is generally 4-5 lbs total.

The only real con I have with a hammock setup is that people constantly criticize me for using it. I just got back from a weekend training in the hills (I am a SAR volunteer and our trainings involve a lot of camping) - it was supposed to be in the mid 40s, and an elderly trainer looked at my Blackbird and announced loudly that I was going to be cold in it. I told him I'd used it for a couple years and if anything I would be warmer than I wanted to be - and I was, because I brought the wrong top quilt, and ended up sweating through the night. Next morning he said I was cold, wasn't I? He did not believe me when I told him how warm it got. Later in the day he softened up some and asked a few questions about it. I told him the truth - I hate being cold, and if I had gotten cold, I would have either been climbing in a tent with someone or getting in my car and turning on the heater! Most of the reason I went to hammocks was being able to sleep through the night, the rest of my reasons have to do with being cold - the discomfort of being on the ground on the thin pad makes me thrash in my sleep, and the end result is usually winding up off the pad, and cold.

My most versatile combo is the hammock, tarp, a pad and a top quilt - I can hang, tarp or use the hammock as a bug bivy with the tarp. I very much prefer the hammock, as you can guess.