Stephen,
Unless you're pitching in conditions that require a certain double-walled tent (snow loading, very high winds) there is little to be gained by going to double-walled route, outside of sentimental or emotional attachment to this style of shelter (and there's nothing wrong with that!).
Going right to a single wall, tarp tent-style shelter is one of those leaps of faith. There's a lot to be gained in terms of less weight and more function by using a non-freestanding single wall tent. It might require creative pitching if you find yourself entirely on slickrock or an AT tent platform, but its certainly manageble. Most current tarp tent designs eliminate almost all contact with the tent walls and can be pitched to withstand very gusty conditions.
Just this past weekend I pitched my tent on a hard packed gravel and dirt campsite and a raised sandy berm in the middle of a creek..talk about one extreme to the other! One site broke an Easton aluminum tubular stake, the other required piling rocks on top of the stakes to hold them in place. At some point during the latter pitch, I got rain and gusts that had to be over 30 mph. The tent held fine.
Don't be afraid to experiment with this style of tent. My Contrail is one of the few pieces of equipment I own that I felt comfortable buying site-unseen. And, if you end up deciding its just not for you, most tarp tents have an excellent resale value. You're not likely to lose more than 10% on a nearly new Tarptent.