This is a great site, and - having little idea what I am doing - I've already learned quite a lot from y'alls posts. Many thanks.

I'm a pudgy newbie with some long past experience in the outdoors. I'd like to get back out there. So, clearly the hammock is the way to go. I remember a childhood of tents: of jagged rocks, uneven ground and - at best - pebbly beaches. Oh do I remember it. But I'm at a place now in my life to give camping a second more-successful shot. Why? To connect to my past and to experience some sereneness outside the confines of Buddhist meditation halls. But I have pretty specific needs and scant experience. Could you please help guide me in purchasing a hammock?

Here's my criteria:
---I'm a big guy. 32 y.o., 6'3", 270 lbs (+/-10?). I'm in good shape. Run 4 miles on treadmill and bike 30 mins in gym twice per week. I've completed a couple of marathons and olympic triathlons. But I'm what they lovingly call "a Clydesdale."
---I have pretty severe sleep apnea (I'm big). It does not deprive me of oxygen, only a good night's sleep. Therefore, I have real trepidations about going outside my bedroom set-up. I like a fan to blow constantly over me, but I figure I can do without this. Oh, and I will bring my absolutely not-camping-approved nightly pillow. Sleep is about the most important commodity to me, and it is what buying a hammock is all about as well (coincidence?).
---I sleep on my side, I sleep on my side, I sleep on my side. Did I mention... Seriously, I NEVER sleep in another position. Two choices: left or right side.
---I've only ever done sissy car camping with day hikes, and right now I can really only see myself repeating this. I was a sea scout, which means we car camped with boats. I also spent a couple young summers in Santa Cruz at a month long sleepaway camp. I'm not a complete idiot in the wilderness, but I'm pretty close. I live in Brooklyn, NY ("The Big Up Yours!") and I am definitely a city mouse. There are no single story buildings within four blocks of me. But I'm also a Crisis Intervention Teacher for emotionally disturbed students in Harlem. Its exactly what it sounds like. Yes, I can take a little pain. I can dodge a knife, but I'm not too good at using one. I can slide over desks, but I wobble over puny trail rocks.
---Gear weight really doesn't matter to me. If/when it does, I'll buy a new rig anyways.
---I won't winter camp. Again, if I change my mind, then I'll pony up for new gear.
---I will camp in the death throes of a Mid-Atlantic/New England summer. Humidity and mosquitoes are a given. Mid spring and and Early fall may be included as well.
---I'm cost agnostic. I intend to sum up the cost of all gear, divide it by $60 (the miniumum cost of a priceline hotel) and the resulting number will be how many days that I will commit to camping with this stuff. More expensive hammock means more days outdoors. I'll do this, then I'll preemptively hang the G.W. "Mission Accomplished" banner and gloat at my success. Of course, I'd also like to spend as little as possible to meet this litany of criteria.
---I intend to take a friend with me who does know what he's doing. I'm dumb, but dumb enough to go it alone. He's one of you UL types that's at home chomping down on a Rambo knife. Yeah, Kurtz'll keep me from doing the colossally stupid. I will compensate his dialing it down for me. I'll buy him lots of beer. Lots of beer.

Thanks in advance for your help. It is as greatly appreciated as it is needed.

-Nate.