Don't feel too bad. Most folks don't know about HF.
As far as middle of the road, what kind of conditions are you looking at? Is it three-seasons use? Will there be a lot of bugs where you're likely to be? Is having a modular system where the weight/bulk/cost of it goes up and down with the seasons worth the hassle for you?
Personally, if you're looking for a moderately-priced hammock without an integral bug net, my recommendations would be either the Warbonnet Traveler with the webbing suspension or the ENO Doublenest, replacing the stock suspension with either the Warbonnet adjustable webbing suspension or Arrowhead Equpment's version of the same. Many folks will tell you to go with whoopie slings, and they will save you some weight. However, the ease of set up with the adjustable webbing is hard to beat.
For a tarp, I'd go with either the Wilderness Logics Tadpole or the Warbonnet Edge tarp, as both give you good coverage under all but cold, blustery conditions without too much weight. They're very user-friendly versus the asymmetric diamond tarps that several companies sell, though the diamond tarps win out on weight. If you're willing to spend for cuben fiber, Hammock Gear makes a wonderful four-season tarp that comes in at under seven ounces and closes at both ends in the $300.00 range. Might be a bit rich for your blood.
For insulation, you can still use your sleeping bag or quilt in the hammock for a topquilt. However, like sleeping on the ground, you need some insulation under you; it's more difficult here, since more of your body is in contact with the hammock than it would be with the ground (one of the secrets of comfort in a hammock). You can either use a double-layer hammock and insert a wide pad into the pocket between layers (the WB Traveler double layer is designed for this) or get an underquilt. There are many quality manufacturers of underquilts, including Hammock Gear, Jacks R Better, Warbonnet, Tree to Tree Trail Gear, and Arrowhead Equipment. Here, it's really dependent upon what temperature ranges you're looking for, how much weight matters to you, and what prices you're willing to shell out for.
If you want a bug net, the two options I'd prefer with a netless hammock are Papa Smurf's bug sock and Warbonnet's Traveler bug net.
Whichever way you go, I highly recommend taking a month or so and looking over the information on Hammock Forums. They're all really welcoming and willing to help with someone looking at hammocks for their sleep system.