icanon,
I"ve read this entire thread and feel I can actually add some clarity. Boon docking is not for everyone. If you have big fears, stay away. If you want to try it, do it in steps to see if it is right for you. It's fun to dream and talk about this stuff, but the best way is to jump right in; make your mistakes; and reaccess.
There are two major issues you face: decide on which style you embody:
1. Are you a go to one spot and stay a while type camper or are you a 'one-night-one-site' camper, moving every day or so. The later is more of a traveller than a camper. This polar opposite difference in style does affect your choices. How long can you realistically stay off-grid? Most of us are limited by the size of our black tank. What about power? Fresh water? Ability to self-extract (aka: get unstuck)?
2. You are only limited by your technique at finding and getting to a remote site and the vehicle's ability and limitations at getting you there. A lot of that is nose, and lot more is experience. Do you think BKA (Bryan) was as good at finding a cool spot for a day or two 7.5 years ago as he is currently? A sidebar on the vehicle limitation is whether you have carry over technique from another interest, like jeeping or off-roading, truck driving, heavy equipment operating, or back packing. I come from a lifetime of off-roading and chose a conveyance that fits well with that paradigm.
I wish I could say, "go as a group with other like-minded people." Alas, every time we've tried that, it was a no-fit. Every time, except with my brother who has a similar background and drives a rig with the same abilities as ours. No one marches to the same drummer you do. You just need to find that drummer.
jefe