How long were most of you guys riding before you started heading out to these areas as opposed to just riding the groomers at the hill?
Off-piste (not out of bounds, but glades, chutes, steeper technical stuff, etc.) and deep powder are very different from groomers at first. The principles are are relatively the same though, so it shouldn't take longer than a couple days to start getting used to riding in real powder, near some trees (riding beside the trees and getting closer and closer is a good way to start as opposed to just diving right in).
One of the skills you have to develop for off-piste riding has nothing to do with the mechanics of riding itself. You have to learn how to pick your line. Reading the run, the snow, the bumps, etc. is something that comes with time. Start on a slope that is generally a little less steep then your current limit on a groomer, but it has a few trees or rocks on it. Pick a line through the "hazards" and try it out. As long as you don't get tunnel vision and focus right on the tree, you'll be fine, and probably have a blast doing so. Repeat again and again with different terrain, getting steeper, more narrow, add in some small drops, then some larger drops.
At some point along the line the mountain becomes your playground. The trees are your dance partners and you gracefully swing around them without missing a beat. The rocks and cliffs are no longer "hazards" but a solid base for snow to form a jump on. Chutes are not scary but a way of deterring the scared away from the beautiful powder pockets awaiting you at the bottom.
No one can tell you how long until you get comfortable in the crazy stuff, you may be ready right now to start learning! I rode for 18 years in Ontario, Quebec, Vermont, New Hampshire, and once at Fernie before I finally moved here. So I was lucky enough to gradually build up to this kind of terrain.
Your learning curve will be steeper, but my GF is riding shit like this now without hesitation, after two full seasons in the Canadian Rockies:
THIS is your playground: