I finally made it back to check the feedback and am impressed by the activity here and all the valuable input! So thanks to everyone who piped in! I'm taking MNpin's advice to heart given what is likely very similar if not identical terrain, nor more than 400ft elevation change but steep stuff. I'll...

Soooo a guy (me) with only downhill and skate xc experience, now wants to ski up down and around the bluffs out my front door in Wisconsin off trail. Tight valley bluff terrain, sandstone cliffs (that I'd love to go off...) and steep grades abound, winding river stream bed valleys. I don't want to p...