Couple of loose thoughts...
1) It is important, as much as possible, to compare apples to apples. In general, AT gear should be compared only the heaviest of tele gear. I'm thinking here of boots like the Scarpa T2 and up and cable and plate bindings and wide skis. I call that stuff heavy tele gear. In contrast, light nordic backcountry gear falls in between xc gear and heavy tele/AT gear. So IMO, these are the 3 major buckets you have to choose from.
+ Light xc gear (best for skiing in nordic tracks)
+ Heavy Tele & AT (good for rough and rugged downhills)
+ Nordic Backcountry (in between the 2 extremes)
2) If you are a really good alpine skier and you take joy in really working a ski, you may find heavy tele to be a fundementally broken approach. You *can* make good p-turns on heavy tele gear, this is very true. But you can't utterly dominate a run on tele gear the way you can with a locked heel. Just mho, anybody who tells you you can rip just as well on tele gear probably hasn't plumbed the depths of what you can do on alpine gear with a fixed heel. If you are a hard charger, AT may be your ticket.
3) I've really mellowed out over the years and really prefer low angled powder turns over high speed skiing. Wisdom or wimp? Regardless, nordic backcountry is much much better for this type of skiing in New England imo. If you are just thinking about matching the gear to the type of skiing you will be doing, you might start here:
http://home.comcast.net/~pinnah/DirtbagPinner/quick-picks.html
4) For somebody looking to make lazy turns in the puckerbush, a good starting point would be Fischer Rebounds, Voile Mountaineer Pins, Garmont Excursions. Lots of great variations off of this basic theme.
5) Regarding the learning curve, I think it depends on whether you are talking about heavy tele or nordic backcountry gear. For the former, rent heavy tele gear and take a few lessons at a ski area. The bigger the boots and the wider the skis, the easier the transition will be, provided you are a decent alpine skier to begin with. If you are not an alpine skier but want to learn heavy tele, I can't in good conscience suggest learning on tele gear. Prolly better to learn alpine first then move to tele.
For nordic backcountry and if you are an alpine skier, my suggestion is to rent xc gear and take lessons at a nordic center learning kick and glide. Nordic backcountry is as much or more about forward motion and striding as it is about turning. Really the only turns you *need* are the snowplow and step turn when in the woods.
Hope this helps,