On trail/Off trail-How do you feel about it?

Here's a photo in which we're coming down the chute from Rachel to Martin Lake in the Beartooths. Notice the concerned look on my face. We spent about 30 min scouting it out. One of the TRs had said the best way was up through some trees on the right, but to us, it looked easier to go straight down the chute, which is what we did. We made it down without any problem.
How do you feel when hiking off-trail? Sometimes there's a well defined use trail, or a procession of cairns. Sometimes there's just the faintest suggestion of a path through the grass, which ends at the boulder field. Sometimes the talus is small, and easy to traverse, other times the boulders are big and scary, and you're happy to reach one with a flat top so you can catch your breath.
Coming around a lake by a cliff should you stay close to the water, and hope you have a few rocks, or at least 18" of ground to inch your way around, or go up and over. And when you do go over you look down and think "hmmm, I don't know about this". But as you continue to look, you see a couple of handholds and spots to step and you make your way down. Or your buddy's ahead and when he gets to the top you call out "How's it look?", and he says "It's do-able!", and you're happy.
Should we go left around this little rise or right? When you looked at the map at home, sitting on the couch, that area appeared as flat as a soccer field. But it's not. Then you look over your shoulder at what was a perfectly blue sky and you wonder 'Is that just haze, or are those clouds, and are they getting darker?"
For me, at least, it's always a bit concerning. Even when I've read trip reports about the route, and looked at pictures, and gone on Google earth, there's always a bit of uncertainty. Plus, I'm talking about above treeline stuff, I'm sure it's more difficult in the woods.
But you make your way through that endless field of car-sized boulders, and the way around the hill was correct, you see a bootprint, and the chute was not too steep, and a little ways up you come across a nice, grassy bench above a stream or lake. An absolutely pristine, perfect camp. There's no one else around, because it just ain't that easy to get to. That makes it worth it.