Good advice so far. Definitely try before you buy.
First there are two basic types of hammocks: gathered end (the majority) where you have to sleep on a diagonal to get nearly flat, and bridge hammocks which have spreader bars and you lay down the middle and are (at least my opinion) much flatter.
If you go with a gathered end an underquilt is a much more manageable way to insulate underneath. If you want to stick with your pad, a double layer hammock will help tremendously to keep the pad in place. Otherwise the pad often slips around every time you move. With a bridge, either a pad or UQ will work, but again having a double layer is helpful. FWIW, I hated pads in my gathered end hammocks, but prefer a pad in my bridge hammocks.
I have had 12 hammocks (6 gathered end including ENO, TTTM, Hennesy, and Clark (+2 homemade), and 6 bridge style (4 homemade, one Eureka Chrysalis and one Warbonnet RidgeRunner). I am very much a proponent of the bridge style, though granted they are inherently a little heavier due to the spreader bars (though this can be mitigated in some instances by using carbon fiber poles or (if you use them) hiking poles. Some people dislike bridge hammocks because they feel tippy, but in my experience I found I adapted to this feeling quickly and it was never really an issue. The only purchased hammock I still retain is the WB RidgeRunner.
Ultimately, I no longer hang as 99% of my camping is with my wife and she was not a proponent of hanging due to the lack of "togetherness". So I have a couple hammocks left in the gear closet (one home made no-net gathered end (single layer) and the WB RidgeRunner (netted, double layer bridge). If you'd like to try before you buy and you are a trustworthy fellow (which I have no way to verify, but you hang out here on BPL and are a member (and involved with Scouts) so I would take it on faith), I would be willing to send you both to try out. If you like one (or both) we could make a deal or you can send them back. Unfortunately, I suspect my hanging days are going to be few to none for the foreseeable future, so they might as well find a good home.
If this is of interest to you, shoot me a PM and we can discuss it further.
Don't give up on HF. There is definitely a lot of information and a lot of opinions on what is best. I spent a lot of time in the last 5 years over on HF (same screen name), but rarely check in now days. You really have to try out a few to find out what works for you. Once you decide on a system, then you can play with different tarp set ups, suspensions, insulation and whatnot. One good thing about HF is that if you do buy a hammock and then elect to change to something else, there is usually a good market for resale there.